Hydrazine hydrate (1:1) → 3(R)-amino-2,3-dihydro-1,5(5H)-benzothiazepin-4-one

HRID 980619Notes

Reaction equation

HRID 980619 reaction equation
C1(=O)[N:5]([C@@H:6]2[C:12](=[O:13])[NH:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[S:8][CH2:7]2)C(=O)C2=CC=CC=C12.O.NN>C(O)C>[NH2:5][C@@H:6]1[C:12](=[O:13])[NH:11][C:10]2[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=2[S:8][CH2:7]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 134546823(R)-phthalimido-2,3-dihydro-1,5(5H)-benzothiazepin-4-one

Product 1

HCID 133751443(R)-amino-2,3-dihydro-1,5(5H)-benzothiazepin-4-oneYield 62.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3(R)-phthalimido-2,3-dihydro-1,5-(5H)-benzothiazepin-4-one (10 g), ethanol (500 ml) and hydrazine hydrate (6.2 g) is refluxed for 1 hour. After ethanol is removed by evaporation under reduced pressure, water (300 ml) is added, and the mixture is extracted with ethyl acetate (400 ml). The extract is washed with 0.1 N sodium hydroxide solution (100 ml×2) and water (100 ml) successively, dried over anhydrous magnesium sulfate and concentrated in vacuo to give 3(R)-amino-2,3-dihydro-1,5(5H)-benzothiazepin-4-one (3.75 g) as colorless leaflets.

Workup

  1. temperatureis refluxed for 1 hour
  2. customAfter ethanol is removed by evaporation under reduced pressure, water (300 ml)
  3. additionis added
  4. extractionthe mixture is extracted with ethyl acetate (400 ml)
  5. washThe extract is washed with 0.1 N sodium hydroxide solution (100 ml×2) and water (100 ml) successively
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5669b029bd6242e098e53a92bcc03d4c
Source dataset
uspto-grants-1987_01
Patent number
US04638000

Reaction notes

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