(S)-1-(3,5-Bis(trifluoromethyl)phenyl)ethanamine → 4-Thiazolecarboxamide, N-[5-[[[[(1S)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl]amino]thioxomethyl]amino]-2-pyridinyl]-

HRID 649887Notes

Reaction equation

HRID 649887 reaction equation
[N:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11]([C:13]2[N:14]=[CH:15][S:16][CH:17]=2)=[O:12])=[N:8][CH:9]=1)=[C:2]=[S:3].[CH3:18][C@@H:19]([C:21]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:22]=1)[NH2:20]>C(#N)C>[F:28][C:27]([F:29])([F:30])[C:25]1[CH:26]=[C:21]([C@@H:19]([NH:20][C:2]([NH:1][C:4]2[CH:5]=[CH:6][C:7]([NH:10][C:11]([C:13]3[N:14]=[CH:15][S:16][CH:17]=3)=[O:12])=[N:8][CH:9]=2)=[S:3])[CH3:18])[CH:22]=[C:23]([C:31]([F:32])([F:33])[F:34])[CH:24]=1

Participants

4

Reactant 2

HCID 1512509(S)-1-(3,5-Bis(trifluoromethyl)phenyl)ethanamineHCID 15521613N-(5-isothiocyanato-2-pyridinyl)-1,3-thiazole-4-carboxamide

Product 1

HCID 30100864-Thiazolecarboxamide, N-[5-[[[[(1S)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl]amino]thioxomethyl]amino]-2-pyridinyl]-

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of N-(5-isothiocyanato-2-pyridinyl)-1,3-thiazole-4-carboxamide (0.36 g) and (S)-alpha-methyl-3,5-bis(trifluoromethyl)-benzenemethanamine (0.36 g) is heated with acetonitrile (10 mL) until all solids are dissolved. The solution is allowed to stand for 12 hours. A white solid forms and is collected by filtration (0.40 g). [M+H] 520.

Workup

  1. dissolutionare dissolved
  2. filtrationA white solid forms and is collected by filtration (0.40 g)

Sources & evidence

ORD record
ord-a88d4f5e6876485c859b85abda69babc
Source dataset
uspto-grants-2001_08
Patent number
US06271236B1

Reaction notes

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