Reaction SMILES: IC1C=C(I)C=C(I)C=1C1C=CC(C)=CC=1.[I:17][C:18]1[C:23]([CH2:24][CH3:25])=[C:22]([I:26])[C:21]([CH2:27][CH3:28])=[C:20]([I:29])[C:19]=1[C:30]1[CH:35]=[CH:34][C:33]([C:36](O)=[O:37])=[C:32]([N+:39]([O-:41])=[O:40])[CH:31]=1.S(Cl)([Cl:44])=O>[Zn]>[I:17][C:18]1[C:23]([CH2:24][CH3:25])=[C:22]([I:26])[C:21]([CH2:27][CH3:28])=[C:20]([I:29])[C:19]=1[C:30]1[CH:35]=[CH:34][C:33]([C:36]([Cl:44])=[O:37])=[C:32]([N+:39]([O-:41])=[O:40])[CH:31]=1
Reactant: O=S(Cl)Cl
Reactant: CCc1c(I)c(CC)c(I)c(-c2ccc(C(=O)O)c([N+](=O)[O-])c2)c1I
Agent: Cc1ccc(-c2c(I)cc(I)cc2I)cc1
Agent: [Zn]
Product: CCc1c(I)c(CC)c(I)c(-c2ccc(C(=O)Cl)c([N+](=O)[O-])c2)c1I

Procedure:
Freidel-Crafts acylation is performed on 2′,4′,6′-triiodo-3′-ethyl-3-nitrobiphenyl-4-carboxylic acid (13) in the presence of AlCl3 and CH3COCl to yield 2′,4′,6′-triiodo-3′-ethyl-5′-acetyl-3-nitrobiphenyl-4-carboxylic acid (17). 2′,4′,6′-triiodo-3′-ethyl-5′-acetyl-3-nitrobiphenyl-4-carboxylic acid (17) is then reacted with a zinc mercury amalgam and hydrochloric add and heated to yield 2′,4′,6′-triiodo-3′,5′-bis(ethyl)-3-nitrobiphenyl-4-carboxylic acid (18). C 15 ⁢   ⁢ H 10 ⁢ I 3 ⁢ N ⁢ O 4 ⁢ → C ⁢   ⁢ H 3 ⁢ C ⁢   ⁢ O ⁢   ⁢ Cl Al ⁢   ⁢ Cl 3 ⁢ → Δ Zn ( Hg ) ,   ⁢ H ⁢   ⁢ Cl ⁢ C 17 ⁢   ⁢ H 14 ⁢ I 3 ⁢ N ⁢   ⁢ O 4 2′,4′,6′-triiodo-3′,5′-bis(ethyl)-3-nitrobiphenyl-4-carboxylic acid (18) is reacted with thionyl chloride to yield 2′,4′,6′-triiodo-3′,5′-bis(ethyl)-3-nitrobiphenyl-4-carbonyl chloride (19). C 17 ⁢   ⁢ H 14 ⁢ I 3 ⁢ N ⁢   ⁢ O 4 ⁢ → S ⁢   ⁢ O ⁢   ⁢ Cl 2 ⁢ C 17 ⁢   ⁢ H 13 ⁢ Cl ⁢ I 3 ⁢ N ⁢   ⁢ O 3 1,3,4,6-tetra-O-acetyl-D-glucosamine (9) is reacted with 2′,4′,6′-triiodo-3′5′-bis(ethyl)-3-nitrobiphenyl-4-carbonyl chloride (19) to yield 2-nitro-4-[3′,5′-bis(ethyl)-2′,4′,6′-triiodophenyl]-benzoyl-1,3,4,6-tetra-O-acetyl-D-glucosamine (20). C14H21NO9+C17H13ClI3NO3→C31H33I3N2O12 2-nitro-4-[3′,5′-bis(ethyl)-2′,4′,6′-triiodophenyl]-benzoyl-1,3,4,6-tetra-O-acetyl-D-glucosamine (20) is oxidized with potassium permanganate to yield 2-nitro-4-[3′,5′-bis(carboxylic acid)-2′,4′,6′-triiodophenyl]-benzoyl-1,3,4,6-tetra-O-acetyl-D-glucosamine (21). C 31 ⁢   ⁢ H 33 ⁢ I 3 ⁢ N 2 ⁢   ⁢ O 12 ⁢ → K ⁢   ⁢ Mn ⁢   ⁢ O 4 ⁢ C 29 ⁢   ⁢ H 25 ⁢ I 3 ⁢ N 2 ⁢   ⁢ O 16 2-nitro-4-[3′,5′-bis(carboxylic acid)-2′,4′,6′-triiodophenyl]-benzoyl-1,3,4,6-tetra-O-acetyl-D-glucosamine (21) is reacted with ethanol and weak hydrochloric acid and heated to yield 2-nitro-4-[3′,5′-bis(ethoxycarbonyl)-2′,4′,6′-triiodophenyl]-benzoyl-1,3,4,6-tetra-O-acetyl-D-glucosamine (22). C 29 ⁢   ⁢ H 25 ⁢ I 3 ⁢ N 2 ⁢   ⁢ O 16 ⁢ → Δ Et ⁢   ⁢ O ⁢   ⁢ H ,   ⁢ H ⁢   ⁢ Cl ⁢ C 33 ⁢   ⁢ H 33 ⁢ I 3 ⁢ N 2 ⁢   ⁢ O 16 2-nitro-4-[3′,5′-bis(ethoxycarbonyl)-2′,4′,6′-triiodophenyl]-benzoyl-1,3,4,6-tetra-O-acetyl-D-glucosamine (22) is reacted with methylamine to yield 2-nitro-4-[3′,5′-bis(N-methylcarboxamide)-2′,4′,6′-triiodophenyl]-benzoyl-1,3,4,6-tetra-O-acetyl-D-glucosamine (23). C 33 ⁢   ⁢ H 33 ⁢ I 3 ⁢ N 2 ⁢   ⁢ O 16 ⁢ → C ⁢   ⁢ H 3 ⁢   ⁢ N ⁢   ⁢ H 2 ⁢ C 31 ⁢   ⁢ H 31 ⁢ I 3 ⁢ N 4 ⁢   ⁢ O 14 2-nitro-4-[3′,5′-bis(N-methylcarboxamide)-2′,4′,6′-triiodophenyl]-benzoyl-1,3,4,6-tetra-O-acetyl-D-glucosamine (23) is treated with stannous chloride and hydrochloric acid to yield 2-amino-4-[3′,5′-bis(N-methylcarboxamide)-2′,4′,6′-triiodophenyl]-benzoyl-D-glucosamine (24). C 31 ⁢   ⁢ H 31 ⁢ I 3 ⁢ N 4 ⁢   ⁢ O 14 ⁢ → Sn ⁢   ⁢ Cl 2 ,   ⁢ H ⁢   ⁢ Cl ⁢ C 23 ⁢   ⁢ H 25 ⁢ I 3 ⁢ N 4 ⁢   ⁢ O 8