Reaction SMILES: [CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[NH:10][C:11]([NH:13][C:14]1[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=1[CH3:22])=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.BrBr.CCN(CC)CC.NC(N)=O>C(Cl)Cl.C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[N:10]=[C:11]=[N:13][C:14]1[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=1[CH3:22]
Reactant: Cc1cc(C)c(NC(=O)Nc2c(C)cc(C)cc2C)c(C)c1
Agent: BrBr
Agent: NC(N)=O
Agent: c1ccc(P(c2ccccc2)c2ccccc2)cc1
Solvent: ClCCl
Solvent: CCN(CC)CC
Solvent: ClC(Cl)Cl
Product: Cc1cc(C)c(N=C=Nc2c(C)cc(C)cc2C)c(C)c1
Temperature: 42 °C
Yield: 57.4 %

Procedure:
1,3-Di-(2,4,6-trimethylphenyl)urea (12.0 g, 0.0405 mol, prepared in accordance with Example 6), PPh3 (13.27 g, 0.0506 mol), Br2 (2.07 mL, 6.47 g, 0.0506 mol, diluted for addition with 40 mL CH2Cl2), and Et3N (14.10 mL, 10.24 g, 0.1012 mol) were reacted in a procedure analogous to that described in Example 2, using 400 mL of CH2Cl2 solvent in a 3-necked, 500 mL 24/40 round bottomed flask. The urea did not dissolve in the CH2Cl2 even when the reaction mixture was heated to 42° C. overnight with stirring. The reaction mixture was transferred to a 1 L flask, 500 mL CHCl3 was added, and the CH2Cl2 was removed by distillation at atmospheric pressure. The urea did not dissolve in the CHCl3 even when heated to 60-65° C. The flask was cooled to room temperature, sealed with a septum, and allowed to stir for a period of 10 days, after which no noticeable changes were observed. The mixture was filtered to remove the large quantity of insolubles (presumed to be recovered urea), and the filtrate was extracted with 1×300 mL distilled water, dried over Na2SO4, and depleted of volatiles on a rotary evaporator giving a yellow oil. This oil was extracted with 200 mL petroleum ether, causing precipitation of beige Ph3P═O. Following filtration, the petroleum ether solution was concentrated to about 50 mL, cooled to −20° C. to facilitate precipitation of additional Ph3P═O, and re-filtered. Removal of volatiles from the filtrate gave the crude carbodiimide as a light yellow oil which slowly solidified (6.77 g, 60%). Following Kugelrohr distillation at 120-140° C./0.08 mm Hg, the distilled carbodiimide (6.469 g, 58%) was obtained as a white solid, with a significant aryl-P impurity (CDCl3 1H NMR δ 7.31 ppm (br m); 13C{1H} NMR δ 137.50 (d, JCP=10.6 Hz), 134.03 (d, JCP=19.13 Hz), 132.35 (minor, app t, JCP˜14.4 Hz), 128.99 (s), 128.78 (d, JCP=6.9 Hz)). Recrystallization of the distilled material from minimal petroleum ether at −20° C. (filtering the mother liquor through a Nylon filter prior to cooling) gave chunky colorless crystals (3.823 g, 34%) still containing this impurity. The crystals and residual material from the mother liquor (obtained by removal of volatiles) were eluted in 1.5-2 g batches on silica with 5% v/v toluene in hexanes, using a Cyclograph apparatus (silica disc, thickness 1 cm; spin rate 334 rpm, pump flow rate 2.98 at 0-15 mL/min) to give the pure carbodiimide (Rf of carbodiimide˜ 0.55, Rf of impurity˜ 0.40) (3.051 g, 27%). 1H NMR (CDCl3): δ 6.82 (s, 4H, aryl), 2.33 (s, 12H, o-Me), 2.24 (s, 6H, p-Me). 13C{1H} NMR (CDCl3, assigned by DEPT-135): δ 134.13 and 133.54 (aryl-p and ipso), 132.68 (aryl-o), 129.63 (N═C═N), 129.12 (aryl-m), 21.00 (p-Me), 19.11 (o-Me). IR (thin film on NaCl): 3003 (sh), 2972 (m), 2945 (m), 2918 (m), 2855 (m), 2280 (sh), 2174 (vs), 2064 (sh), 1584 (w), 1476 (s), 1445 (sh), 1377 (w), 1281 (w), 1208 (s), 1146 (m), 1032 (w), 957 (w), 936 (w), 853 (m), 727 (m), 604 (m), 538 (m) cm−1. FD-MS m/z (%): 279.3 (MH+, 100). Exact mass calculated for C19H22N2: 278.18 (molecular weight 279.39 g/mol). Melting point (DSC): onset (extrapolated) 41° C., max. 45° C.