2-Aminothiophenol → HCID 13763165, compound

HRID 1906716Notes

Reaction equation

HRID 1906716 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]=[C:10]([C:15](=O)[CH3:16])[C:11]([O:13][CH3:14])=[O:12].[NH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[SH:27]>CN(C)C=O.C(OCC)(=O)C>[CH3:16][C:15]1[NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[S:27][CH:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[C:2]([F:19])([F:18])[F:1])[C:10]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 2

HCID 87132-AminothiophenolHCID 54428372HCID 54428372, compound

Product 1

HCID 13763165HCID 13763165, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-[[2-(trifluoromethyl)phenyl]methylene]-3-oxobutanoic acid, methyl ester (1.8 g., 6.61 mmole) in dimethylformamide (5 ml.) is treated with 2-aminothiophenol (919 mg., 6.61 mmole) at room temperature. The reaction is stirred at room temperature for about 72 hours. The reaction is then heated at 65°-70° (oil bath temperature) for 10 hours. It is cooled to room temperature and diluted with ethyl acetate (50 ml.). The solution is thoroughly washed with water, sodium bicarbonate, and brine. After drying over anhydrous magnesium sulfate, the solvent is stripped off to give a yellow solid. Recrystallization from isopropyl ether-dichloromethane gives 783 mg. of product as fluffy needles. The mother liquor is purified by flash chromatography (20% ethyl acetate in hexane) and the resulting solid is recrystallized from isopropyl ether-dichloromethane to give 153 g. of additional product. Recrystallization from isopropyl ether-dichloromethane gives an analytically pure sample of 2,5-dihydro-4-methyl-2-[2-(trifluoromethyl)phenyl]-1,5-benzothiazepine-3-carboxylic acid, methyl ester; m.p. 165°-166.5°. TLC (silica gel, hexane: ethyl acetate, 60:40) Rf =0.36.

Workup

  1. temperatureThe reaction is then heated at 65°-70° (oil bath temperature) for 10 hours
  2. temperatureIt is cooled to room temperature
  3. washThe solution is thoroughly washed with water, sodium bicarbonate, and brine
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. customto give a yellow solid
  6. customRecrystallization from isopropyl ether-dichloromethane
  7. customgives 783 mg
  8. customThe mother liquor is purified by flash chromatography (20% ethyl acetate in hexane)
  9. customthe resulting solid is recrystallized from isopropyl ether-dichloromethane
  10. customto give 153 g
  11. customRecrystallization from isopropyl ether-dichloromethane

Sources & evidence

ORD record
ord-54e2b14429db490ebe3ee07703b273d9
Source dataset
uspto-grants-1987_03
Patent number
US04654335

Reaction notes

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