1,1'-Carbonyldiimidazole → HCID 11004640, compound

HRID 1421514Notes

Reaction equation

HRID 1421514 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

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 253877Potassium BromideHCID 178490718HCID 178490718, compound

Product 1

HCID 11004640HCID 11004640, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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, υ=cm-1) 3170, 3057, 1726, 1504, 1277, 1128; 1H NMR (300 MHz, DMSO-d6) δ 3.48 (3H, s), 7.15 (1H, d, J=9.0 Hz), 7.55 (1H, dd, J=8.9 Hz, 2.6Hz), 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)mtz: 438(MH+).

Workup

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

Sources & evidence

ORD record
ord-f7a590afea2145dbb54e3a68fa131708
Source dataset
uspto-grants-2000_06
Patent number
US06077861

Reaction notes

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