Dimethyl Sulfate → HCID 178502626, compound

HRID 1079343Notes

Reaction equation

HRID 1079343 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[C:9]2[CH2:10][NH:11][C:12](=[N:15][OH:16])[CH2:13][S:14][C:8]=2[CH:7]=[CH:6][CH:5]=1.[CH3:17]OS(OC)(=O)=O>C(O)C>[Cl:3][C:4]1[C:9]2[CH2:10][NH:11][C:12](=[N:15][O:16][CH3:17])[CH2:13][S:14][C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 178526326HCID 178526326, compound

Product 1

HCID 178502626HCID 178502626, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 10% aqueous solution of sodium hydroxide (4 ml) was added to a suspension of 6-chloro-3-hydroxyimino-2,3,4,5-tetrahydro-1,4-benzothiazepine (2.29 g, prepared as Example 26 above) in ethanol (150 ml). After 15 minutes dimethylsulphate (1.33 g) was added dropwise to the mixture. The reaction mixture was stirred at room temperature for 22 hours and then the solvent was removed by evaporation at reduced pressure. Purification of the residue by chromatography on a silica gel support using dichloromethane followed by dichloromethane/ethanol (97:3) as successive eluents gave 6-chloro-3-methoxyimino-2,3,4,5-tetrahydro-1,4-benzothiazepine, which was recrystallised from n-hexane. Yield 1.21 g (m.p. 120°-121° C.).

Workup

  1. customthe solvent was removed by evaporation at reduced pressure
  2. customPurification of the residue by chromatography on a silica gel support

Sources & evidence

ORD record
ord-bca41b35f2bd4cf497fcc85b23fbcd88
Source dataset
uspto-grants-1996_12
Patent number
US05580866

Reaction notes

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