N-acetyl-S-(2-aminophenyl)cysteine → 5,1-Benzothiazepine-2-one, 3-acetylamino-

HRID 1719102Notes

Reaction equation

HRID 1719102 reaction equation
[C:1]([NH:4][C@H:5]([C:15]([OH:17])=O)[CH2:6][S:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH2:14])(=[O:3])[CH3:2]>C1(C)C(C)=CC=CC=1>[C:1]([NH:4][CH:5]1[C:15](=[O:17])[NH:14][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[S:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 57145208N-acetyl-S-(2-aminophenyl)cysteine

Product 1

HCID 5393625,1-Benzothiazepine-2-one, 3-acetylamino-Yield 71.7%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

1.2 g of N-acetyl-S-(2-aminophenyl)cysteine was dissolved in 20 ml of xylene and the resulting solution was heated under reflux for 2 hours. After cooling, the precipitated crystals were separated and washed with methanol to obtain 0.8 g of the desired compound, or 3-acetylamino-2,3-dihydro-1,5-benzothiazepin-4(5H)-one. Its melting point was 283°-286° C.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter cooling
  4. customthe precipitated crystals were separated
  5. washwashed with methanol

Sources & evidence

ORD record
ord-69814e6d39a44174a436f6162e7f9839
Source dataset
uspto-grants-1985_09
Patent number
US04539151

Reaction notes

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