Sodium Hydroxide Catalyzed N-Alkylation of (Hetero) Aromatic Primary Amines and N1,C5-Dialkylation of 4-Phenyl-2-aminothiazoles with Benzyl Alcohols
Ramachandra Reddy Donthiri; Venkatanarayana Pappula; Darapaneni Chandra Mohan; Hiren H. Gaywala; Subbarayappa Adimurthy; Journal of Organic Chemistry 78 (2013) 6775–6781; doi:10.1021/jo400834h

data_4028399
_publ_section_title
;
 Sodium Hydroxide Catalyzed N-Alkylation of (Hetero) Aromatic Primary
 Amines and N1,C5-Dialkylation of 4-Phenyl-2-aminothiazoles with Benzyl
 Alcohols
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6775
_journal_page_last               6781
_journal_paper_doi               10.1021/jo400834h
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C54 H52 Cl4 N4 S2'
_chemical_formula_weight         962.92
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.607(4)
_cell_angle_beta                 90.794(4)
_cell_angle_gamma                99.582(4)
_cell_formula_units_Z            2
_cell_length_a                   9.663(3)
_cell_length_b                   10.404(3)
_cell_length_c                   24.867(6)
_cell_measurement_reflns_used    2.48
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      8345
_cell_measurement_theta_min      26.56
_cell_volume                     2464.6(12)
_computing_cell_refinement       'BRUKER SMART'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics    ORTEP
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0475
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            20418
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.64
_exptl_absorpt_coefficient_mu    0.366
_exptl_absorpt_correction_T_max  0.9956
_exptl_absorpt_correction_T_min  0.8919
_exptl_absorpt_correction_type   MULTI-SACN
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       PLATES
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.442
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     591
_refine_ls_number_reflns         10545
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0655
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0866P)^2^+1.9828P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1650
_refine_ls_wR_factor_ref         0.1719
_reflns_number_gt                8901
_reflns_number_total             10545
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400834h_si_001.cif
_cod_data_source_block           531rrfm
_cod_original_cell_volume        2464.7(11)
_cod_database_code               4028399