Hydrochloric Acid → 4-Acetyl-6-chloro-2,3,4,5-tetrahydro-1,4-benzothiazepine

HRID 1079324Notes

Reaction equation

HRID 1079324 reaction equation
[Cl:1][C:2]1[C:7]2[CH2:8][NH:9][CH2:10][CH2:11][S:12][C:6]=2[CH:5]=[CH:4][CH:3]=1.Cl.[C:14](OC(=O)C)(=[O:16])[CH3:15]>>[C:14]([N:9]1[CH2:8][C:7]2[C:2]([Cl:1])=[CH:3][CH:4]=[CH:5][C:6]=2[S:12][CH2:11][CH2:10]1)(=[O:16])[CH3:15]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 101981056-Chloro-2,3,4,5-tetrahydro-1,4-benzothiazepine

Product 1

HCID 98376804-Acetyl-6-chloro-2,3,4,5-tetrahydro-1,4-benzothiazepine

Procedure

A solution of 6-chloro-2,3,4,5-tetrahydro-1,4-benzothiazepine (1.6 g, prepared in a similar manner to its hydrochloride, Example 1 above) in acetic anhydride (15 ml) was stirred at room temperature for one hour. The reaction mixture was poured into ice and extracted with dichloromethane. The organic layer was dried and the solvent was removed by evaporation to give 4-acetyl-6-chloro-2,3,4,5-tetrahydro-1,4-benzothiazepine, which was recrystallised from hexane. Yield 1.68 g (m.p. 79°-81° C.).

Workup

  1. additionThe reaction mixture was poured into ice
  2. extractionextracted with dichloromethane
  3. customThe organic layer was dried
  4. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-301c65891e2b48c9899050c466b29565
Source dataset
uspto-grants-1996_12
Patent number
US05580866

Reaction notes

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