2-Aminothiophenol → HCID 13763166, compound

HRID 1906718Notes

Reaction equation

HRID 1906718 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[C:11]([C:16](=O)[CH3:17])[C:12]([O:14][CH3:15])=[O:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[SH:26]>CN(C)C=O.CCOCC>[CH3:17][C:16]1[NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[S:26][CH:10]([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[C:11]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 2

HCID 87132-AminothiophenolHCID 53677993HCID 53677993, compound

Product 1

HCID 13763166HCID 13763166, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-[(4-nitrophenyl)methylene]-3-oxobutanoic acid, methyl ester (1.295 g., 5 mmoles) in dimethylformamide (5 ml.) is treated with 2-aminothiophenol (695 mg. of 90%, 5 mmoles). After stirring the reaction at room temperature for one hour, it is heated at 60°-65° for 24 hours. The reaction is allowed to cool down to ambient temperature and diluted with ether. The resulting yellow solution is washed thoroughly with water, 1N sodium hydroxide, and brine. After drying over anhydrous magnesium sulfate, the solvent is stripped off to give a yellow foam (1.3 g.). This product is purified by flash chromatography (20% ethyl acetate in hexane) and the residue is recrystallized from isopropyl ether-dichloromethane to provide 2,5-dihydro-4-methyl-2-(4-nitrophenyl)-1,5-benzothiazepine-3-carboxylic acid, methyl ester as yellow needles; m.p. 149.5°-151.5° (sinters at 140°). TLC (silica gel; acetone:hexane, 30:70) Rf =0.30.

Workup

  1. customthe reaction at room temperature for one hour
  2. temperatureit is heated at 60°-65° for 24 hours
  3. washThe resulting yellow solution is washed thoroughly with water, 1N sodium hydroxide, and brine
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. customto give a yellow foam (1.3 g.)
  6. customThis product is purified by flash chromatography (20% ethyl acetate in hexane)
  7. customthe residue is recrystallized from isopropyl ether-dichloromethane

Sources & evidence

ORD record
ord-e6bd6b7883ae42749d8a76f0cc13f1bb
Source dataset
uspto-grants-1987_03
Patent number
US04654335

Reaction notes

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