Triethylamine → HCID 11475465, compound

HRID 397294Notes

Reaction equation

HRID 397294 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[NH:5][N:4]=[C:3]1[S:8][C:9]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O.[C:22]1(=[O:29])[CH2:27][CH2:26][CH2:25][C:24](=[O:28])[CH2:23]1.C1(N=C=NC2CCCCC2)CCCCC1.C(N(CC)CC)C.C[Si](C#N)(C)C>>[CH3:1][N:2]1[C:6](=[O:7])[NH:5][N:4]=[C:3]1[S:8][C:9]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:10]=1[C:11]([CH:23]1[C:24](=[O:28])[CH2:25][CH2:26][CH2:27][C:22]1=[O:29])=[O:13]

Participants

6

Reactant 5

HCID 8471TriethylamineHCID 104341,3-CyclohexanedioneHCID 10868DicyclohexylcarbodiimideHCID 82115Trimethylsilyl cyanideHCID 11151318HCID 11151318, compound

Product 1

HCID 11475465HCID 11475465, compoundYield 68%

Conditions

Temperature
20 °C

Procedure

A mixture of 0.80 g (2.5 mmol) of 2-[(4-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-sulphanyl]-4-trifluoromethyl-benzoic acid, 0.28 g (2.5 mmol) of 1,3-cyclohexanedione and 0.63 g (3.1 mmol) of N,N′-dicyclohexylcarbodiimide is stirred at room temperature (approximately 20° C.) for 48 hours. 0.7 ml (5 mmol) of triethylamine and a drop of trimethylsilyl cyanide are then added, and the mixture is stirred for a further 24 hours. The mixture is then concentrated under water pump vacuum and the residue is stirred with 10% strength aqueous sodium carbonate solution. The mixture is then filtered and the filtrate is washed twice with diethyl ether, acidified with 2N hydrochloric acid and extracted with dichloromethane. The organic phase is dried over magnesium sulphate and the solvent is removed under reduced pressure, giving 0.7 g (68% of theory) of 2-[2-[(4-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-sulphanyl]-4-trifluoromethyl-benzoyl]-1,3-cyclohexanedione as an oil (log P=2.00).

Workup

  1. stirringthe mixture is stirred for a further 24 hours
  2. concentrationThe mixture is then concentrated under water pump vacuum
  3. stirringthe residue is stirred with 10% strength aqueous sodium carbonate solution
  4. filtrationThe mixture is then filtered
  5. washthe filtrate is washed twice with diethyl ether
  6. extractionextracted with dichloromethane
  7. dry with materialThe organic phase is dried over magnesium sulphate
  8. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-2c5942467ce147dc80afc976c745f6bc
Source dataset
uspto-grants-2003_08
Patent number
US06610631B1

Reaction notes

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