Methylamine → 4-[3-(4-Cyano-3-trifluoromethylphenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]-N-methylbenzamide

HRID 1927362Notes

Reaction equation

HRID 1927362 reaction equation
CO[C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([CH3:16])([CH3:15])[C:13](=[O:17])[N:12]([C:18]3[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[C:20]([C:26]([F:29])([F:28])[F:27])[CH:19]=3)[C:11]2=[S:30])=[CH:6][CH:5]=1.[CH3:32][NH2:33]>>[C:24]([C:21]1[CH:22]=[CH:23][C:18]([N:12]2[C:13](=[O:17])[C:14]([CH3:15])([CH3:16])[N:10]([C:7]3[CH:8]=[CH:9][C:4]([C:3]([NH:33][CH3:32])=[O:31])=[CH:5][CH:6]=3)[C:11]2=[S:30])=[CH:19][C:20]=1[C:26]([F:29])([F:28])[F:27])#[N:25]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 15951526HCID 15951526, compound

Product 1

HCID 159515274-[3-(4-Cyano-3-trifluoromethylphenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]-N-methylbenzamideYield 51%

Procedure

A mixture of 4-[3-(4-cyano-3-trifluoromethylphenyl)-5,5-dimethyl-4-oxo-2-thioxo-imidazolidin-1-yl]benzoic acid methyl ester (49c) (0.02 g, 0.0435 mmol) and methylamine (2 ml distilled from its 40% aqueous solution) was kept at −20° C. for 15 hours. After evaporation of the methylamine, the mixture was chromatographed (dichloromethane:acetone, 80:20) to yield 4-[3-(4-cyano-3-trifluoromethylphenyl)-5,5-dimethyl-4-oxo-2-thioxo-imidazolidin-1-yl]-N-methylbenzamide (49d) [RD153] (0.01 g, 0.0224, 51%), the structure of which is illustrated in Formula 20. The ester 4-[3-(4-cyano-3-trifluoromethylphenyl)-5,5-dimethyl-4-oxo-2-thioxo-imidazolidin-1-yl]benzoic acid methyl ester (49c) (0.08 g, 0.0179 mmol, 41%) was also recovered.

Workup

  1. customAfter evaporation of the methylamine
  2. customthe mixture was chromatographed (dichloromethane:acetone, 80:20)

Sources & evidence

ORD record
ord-dab23dc51da54ab89808de980315050b
Source dataset
uspto-grants-2012_05
Patent number
US08183274B2

Reaction notes

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