2-Aminothiophenol → HCID 13763167, compound

HRID 1906717Notes

Reaction equation

HRID 1906717 reaction equation
[C:1]1([CH:7]=[C:8]([C:13](=O)[CH3:14])[C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[SH:23]>CN(C)C=O.CCOCC>[CH3:14][C:13]1[NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[S:23][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]=1[C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 2

HCID 87132-AminothiophenolHCID 2884254Methyl 2-benzylideneacetoacetate

Product 1

HCID 13763167HCID 13763167, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-[(phenyl)methylene]-3-oxobutanoic acid, methyl ester (13.0 g., 63.7 mmole) in dry dimethylformamide (20 ml.) is treated dropwise with 2-aminothiophenol (8.85 g. of 90%, 63.7 mmole). A slight release of heat is noted. The reaction is stirred at room temperature for 6 hours and then heated at 65° for 72 hours. It is cooled to room temperature and diluted with ether. The resulting solution is thoroughly washed with water, sodium bicarbonate and brine. After drying over anydrous magnesium sulfate, the solvent is stripped off to give a yellow solid. It is triturated with isopropyl ether and filtered off to provide 6.93 g. of light yellow crystals. Recrystallization from isopropyl ether-dichloromethane gives an analytically pure sample of 2,5-dihydro-4-methyl-2-phenyl-1,5-benzothiazepine-3-carboxylic acid, methyl ester; m.p. 154°-156°. TLC(silica gel, hexane:acetone, 70:30) Rf =0.35.

Workup

  1. temperatureA slight release of heat
  2. temperatureheated at 65° for 72 hours
  3. temperatureIt is cooled to room temperature
  4. washThe resulting solution is thoroughly washed with water, sodium bicarbonate and brine
  5. dry with materialAfter drying over anydrous magnesium sulfate
  6. customto give a yellow solid
  7. customIt is triturated with isopropyl ether
  8. filtrationfiltered off
  9. customto provide 6.93 g
  10. customRecrystallization from isopropyl ether-dichloromethane

Sources & evidence

ORD record
ord-e5cd192ec9e54dd0baa06693071d8405
Source dataset
uspto-grants-1987_03
Patent number
US04654335

Reaction notes

Loading…