Ammonia → 3-Amino-2-(p-chlorophenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetamide

HRID 345151Notes

Reaction equation

HRID 345151 reaction equation
[NH2:1][CH:2]1[C:8](=[O:9])[N:7]([CH2:10][C:11](OCC)=[O:12])[C:6]2[CH:16]=[CH:17][CH:18]=[CH:19][C:5]=2[S:4][CH:3]1[C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1.[NH3:27]>CO>[NH2:1][CH:2]1[C:8](=[O:9])[N:7]([CH2:10][C:11]([NH2:27])=[O:12])[C:6]2[CH:16]=[CH:17][CH:18]=[CH:19][C:5]=2[S:4][CH:3]1[C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 19993592Ethyl 3-amino-2-(p-chlorophenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate

Product 1

HCID 146486333-Amino-2-(p-chlorophenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 200 ml of methanol is dissolved 1.5 g of ethyl 3-amino-2-(p-chlorophenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate, and ammonia gas is blown into the solution under ice-cooling up to the saturated state. The reaction temperature is slowly elevated to room temperature, and the reaction mixture is left standing overnight. Then, the reaction mixture is concentrated under reduced pressure. Ethyl acetate is added to the obtained residue, and the resulting crystals are collected by filtration to give 0.9 g of 3-amino-2-(p-chlorophenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetamide, m.p. 217-220° C. (decomposition).

Workup

  1. temperaturecooling up to the saturated state
  2. customis slowly elevated to room temperature
  3. waitthe reaction mixture is left
  4. concentrationThen, the reaction mixture is concentrated under reduced pressure
  5. additionEthyl acetate is added to the obtained residue
  6. filtrationthe resulting crystals are collected by filtration

Sources & evidence

ORD record
ord-c03c649da04a42e48666a8b9e478d508
Source dataset
uspto-grants-1991_10
Patent number
US05055464

Reaction notes

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