1-Chloro-4-isothiocyanato-2-(trifluoromethyl)benzene → 1-[4-(2-Benzimidazolylthio)phenyl]-3-(4-chloro-3-trifluoromethylphenyl)thiourea

HRID 2395335Notes

Reaction equation

HRID 2395335 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[NH:12][C:13]3[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=3[N:15]=2)=[CH:6][CH:5]=1)([O-])=O.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[S:29])=[CH:23][C:22]=1[C:30]([F:33])([F:32])[F:31]>C(OCC)(=O)C.[Pd]>[N:15]1[C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[NH:12][C:11]=1[S:10][C:7]1[CH:8]=[CH:9][C:4]([NH:1][C:28]([NH:27][C:24]2[CH:25]=[CH:26][C:21]([Cl:20])=[C:22]([C:30]([F:33])([F:31])[F:32])[CH:23]=2)=[S:29])=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 5200261-Chloro-4-isothiocyanato-2-(trifluoromethyl)benzeneHCID 126176252-[(4-Nitrophenyl)sulfanyl]-1H-benzimidazole

Product 1

HCID 537366441-[4-(2-Benzimidazolylthio)phenyl]-3-(4-chloro-3-trifluoromethylphenyl)thioureaYield 5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-(4-Nitrophenylthio)benzimidazole (5.0 mmoles, 1.37 g) was reduced in ethyl acetate over 1.37 g 5% Pd/C, filtered and condensed and then reacted with 4-chloro-3-trifluoromethylphenylisothiocyanate (5.0 mmoles, 1.0 g) according to procedure C to yield the title compound 0.12 g, 5% product. Mass Spec (FD) 479. Calculated for C21H14ClF3N4 S2 : C, 52.66; H, 2.95; N, 11.70. Found: C, 52.85; H, 3.18; N, 10.47.

Workup

  1. filtrationfiltered
  2. customcondensed

Sources & evidence

ORD record
ord-175c5f26d71a4cbdb380399ed9a892fb
Source dataset
uspto-grants-1998_09
Patent number
US05814646

Reaction notes

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