Dimethyl Sulfate → HCID 178502625, compound

HRID 1079342Notes

Reaction equation

HRID 1079342 reaction equation
COS([O:6][CH3:7])(=O)=O.O[N:9]=[C:10]1[NH:16][CH2:15][C:14]2[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=2[S:12][CH2:11]1.[OH-].[Na+]>C(O)C>[CH3:7][O:6][N:9]=[C:10]1[NH:16][CH2:15][C:14]2[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=2[S:12][CH2:11]1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 178526325HCID 178526325, compound

Product 1

HCID 178502625HCID 178502625, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dimethylsulphate (1.26 g) was added dropwise to a vigorously stirred suspension of 3-hydroxyimino-2,3,4,5-tetrahydro-1,4-benzothiazepine (2 g, prepared in a similar manner to Example 25 above) in a mixture of a 10% aqueous solution of sodium hydroxide (4 ml) and ethanol (150 ml). The reaction mixture was kept at room temperature for 24 hours and then extracted with dichloromethane. The organic layer was dried and the solvent was removed by evaporation. Purification of the solid residue by flash chromatography using dichloromethane as eluent gave 3-methoxyimino-2,3,4,5-tetrahydro-1,4-benzothiazepine, which was recrystallised from hexane. Yield 1.51 g (m.p. 101°-102° C.).

Workup

  1. customprepared in a similar manner to Example 25 above)
  2. extractionextracted with dichloromethane
  3. customThe organic layer was dried
  4. customthe solvent was removed by evaporation
  5. customPurification of the solid residue by flash chromatography

Sources & evidence

ORD record
ord-195863ce33a44b4c9dadb615fd2d078f
Source dataset
uspto-grants-1996_12
Patent number
US05580866

Reaction notes

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