Triethylamine → HCID 86620010, compound

HRID 2074124Notes

Reaction equation

HRID 2074124 reaction equation
[CH:1]1[N:5]=[CH:4][N:3]([C:6](N2C=NC=C2)=[S:7])[CH:2]=1.[N:13]1([C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]([F:30])([F:29])[F:28])=[O:20])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(N(CC)CC)C>ClCCl>[N:3]1([C:6]([N:16]2[CH2:17][CH2:18][N:13]([C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]([F:28])([F:30])[F:29])=[O:20])[CH2:14][CH2:15]2)=[S:7])[CH:2]=[CH:1][N:5]=[CH:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 802641,1'-ThiocarbonyldiimidazoleHCID 167337841-[2-(Trifluoromethyl)benzoyl]piperazine

Product 1

HCID 86620010HCID 86620010, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-Thiocarbonyldiimidazole (2.14 g, 11.4 mmol) was added to the mixture of piperazin-1-yl-(2-trifluoromethylphenyl)methanone (3.36 g, 11.40 mmol) and triethyl amine (1.75 mL, 12.5 mmol) in 50 mL of dichloromethane at 0° C. The mixture was warmed up to room temperature and then stirred at room temperature overnight. The reaction mixture was washed with brine (2×15 mL), dried over anhydrous Na2SO4, concentrated to give the light yellow foam. The crude compound was triturated by anhydrous ether to afford [4-(imidazole-1-carbothioyl)piperazin-1-yl]-(2-trifluoromethylphenyl)methanone as a white solid in 96% yield (4.40 g).

Workup

  1. washThe reaction mixture was washed with brine (2×15 mL)
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customto give the light yellow foam
  5. customThe crude compound was triturated by anhydrous ether

Sources & evidence

ORD record
ord-ae64e1fe8ffe4f73b606cdb693ce250c
Source dataset
uspto-grants-2011_04
Patent number
US07919496B2

Reaction notes

Loading…