Stearoyl chloride → HCID 15069600, compound

HRID 1463470Notes

Reaction equation

HRID 1463470 reaction equation
[C:1](Cl)(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:21]1([C:27]2[S:28][C:29]3[NH:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]=3[N:36]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(CC)CC)C>C1COCC1>[C:21]1([C:27]2[S:28][C:29]3[N:30]([C:1](=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:31][CH2:32][CH2:33][CH2:34][C:35]=3[N:36]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 8212Stearoyl chlorideHCID 8471TriethylamineHCID 9991469HCID 9991469, compound

Product 1

HCID 15069600HCID 15069600, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Stearoyl chloride (4.65 ml) was added dropwise to a mixture of 2-phenyl-5,6,7,8-tetrahydro-4H-thiazolo[5,4-b]-azepine (2.65 g), triethylamine (2.26 ml) and THF (30 ml) under ice-cooling and stirring. After completing addtion dropwise, the mixture was stirred for 1.5 hrs. at room temperature and distilled under reduced pressure to remove the solvent. The residue was extracted with chloroform, and the extract was washed with water, dried and distilled to remove the solvent. The residue was purified by a column chromatography on silica gel to give the title compound (4.31 g, 76%).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 1.5 hrs
  3. distillationat room temperature and distilled under reduced pressure
  4. customto remove the solvent
  5. extractionThe residue was extracted with chloroform
  6. washthe extract was washed with water
  7. customdried
  8. distillationdistilled
  9. customto remove the solvent
  10. customThe residue was purified by a column chromatography on silica gel

Sources & evidence

ORD record
ord-aecd478ce55b47308fadbb843c4f1b82
Source dataset
uspto-grants-1994_04
Patent number
US05300639

Reaction notes

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