Triethylamine → HCID 86609852, compound

HRID 1927312Notes

Reaction equation

HRID 1927312 reaction equation
C(N(CC)CC)C.[N:8]([C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13]([C:19]([F:22])([F:21])[F:20])[CH:12]=1)=[C:9]=[S:10].[C:23]([O:27][C:28](=[O:42])[NH:29][C:30]1[CH:35]=[CH:34][C:33]([NH:36][C:37]([C:40]#[N:41])([CH3:39])[CH3:38])=[CH:32][CH:31]=1)([CH3:26])([CH3:25])[CH3:24].C(OCC)C.CC(C)=O>C1COCC1>[C:23]([O:27][C:28](=[O:42])[NH:29][C:30]1[CH:35]=[CH:34][C:33]([N:36]2[C:37]([CH3:39])([CH3:38])[C:40](=[NH:41])[N:8]([C:11]3[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13]([C:19]([F:20])([F:22])[F:21])[CH:12]=3)[C:9]2=[S:10])=[CH:32][CH:31]=1)([CH3:26])([CH3:24])[CH3:25]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 116155404-Isothiocyanato-2-(trifluoromethyl)benzonitrileHCID 21584533Acetone diethyletherHCID 67134597HCID 67134597, compound

Product 1

HCID 86609852HCID 86609852, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (0.202 g, 2 mmol) was added to a solution of 1a (0.456 g, 2 mmol) and 2b (0.57 g, 2 mmol) in dry THF (5 ml). The reaction mixture was stirred at room temperature for 15 h and then concentrated to yield a dark residue which was subjected to flash chromatography (ethyl ether/acetone, 97:3) to afford {4-[3-(4-cyano-3-trifluoromethylphenyl)-4-imino-5,5-dimethyl-2-thioxo-imidazolidin-1-yl]phenyl}carbamic acid tert-butyl ester, (2c) (0.15 g, 0.3 mmol, 15%).

Workup

  1. concentrationconcentrated
  2. customto yield a dark residue which

Sources & evidence

ORD record
ord-2474761064fa43208f8ef4c27b04f92f
Source dataset
uspto-grants-2012_05
Patent number
US08183274B2

Reaction notes

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