1,1'-Carbonyldiimidazole → HCID 11004640, compound

HRID 362454Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:26][CH3:27])=[C:6]([NH:8][C:9]([C:12]2[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[C:14]([C:22]([F:25])([F:24])[F:23])[CH:13]=2)=[N:10][NH2:11])[CH:7]=1.[C:28](N1C=CN=C1)(N1C=CN=C1)=[O:29].[K+].[Br-]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:26][CH3:27])=[C:6]([N:8]2[C:9]([C:12]3[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[C:14]([C:22]([F:23])([F:24])[F:25])[CH:13]=3)=[N:10][NH:11][C:28]2=[O:29])[CH:7]=1

Participants

Conditions

Temperature: 24 °C

Procedure

N-(5-Chloro-2-methoxyphenyl)-3,5-bis(trifluoromethyl) benzene carbohydrazonamide (4 g, 9.7 mmol) was taken up in THF (600 ml) under N2, and 1,1'-carbonyldiimidazole (1.9 g, 11.72 mmol) added. The solution was stirred for 18 h at 24° C. before solvent was removed by rotary evaporation. The residue was taken up in ethyl acetate (400 ml) and washed with 0.1N HCl solution (100 ml), water (100 ml) and brine prior to drying over MgSO4. Recrystallization from acetonitrile gave 2.92 g (68.6%) mp 205.5°-207° C. IR(KBr, ν=cm-1) 3170, 3057, 1726,1504, 1277, 1128; 1H NMR (300 MHz, DMSO-d6) δ3.48 (3H, s), 7.15 (1H, d, J=9.0 Hz), 7.55 (1H, dd, J=8.9 Hz, 2.6 Hz), 7.69 (1H, d, J=2.6 Hz), 7.87 (2H, br.s), 8.17 (1H, br.s), 12.50 (1H, br.s); MS(DCl)m/z: 438(MH+). Anal. calcd. for C17H10ClF6N3O2 : C, 46.65; H, 2.30; N, 9.60. Found: C, 46.71; H, 2.20; N, 9.60.

Workup

customwas removed by rotary evaporation
washwashed with 0.1N HCl solution (100 ml), water (100 ml) and brine
dry with materialto drying over MgSO4
customRecrystallization from acetonitrile
customgave 2.92 g (68.6%) mp 205.5°-207° C

Sources & evidence

ORD record: ord-ae5e8211de8d40d38dd8fe7a9345c62a
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05869509

Reaction notes

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