Water → 6-chloro-4-methyl-4,5-dihydro-1,4-benzothiazepin-3(2H)-one

HRID 1079319Notes

Reaction equation

HRID 1079319 reaction equation
[Cl:1][C:2]1[C:7]2[CH2:8][NH:9][C:10](=[O:13])[CH2:11][S:12][C:6]=2[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:16]I.O>CS(C)=O>[Cl:1][C:2]1[C:7]2[CH2:8][N:9]([CH3:16])[C:10](=[O:13])[CH2:11][S:12][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 102200036-Chloro-4,5-dihydro-1,4-benzothiazepin-3(2H)-one

Product 1

HCID 233666996-chloro-4-methyl-4,5-dihydro-1,4-benzothiazepin-3(2H)-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of 6-chloro-4,5-dihydro-1,4-benzothiazepin-3(2H)-one (5.33 g, prepared in a similar manner to example 11 of international patent application WO 92/21668) in dry dimethylsulphoxide (60 ml) was added slowly at room temperature to a stirred suspension of sodium hydride (0.6 g) in dimethylsulphoxide (20 ml). After the addition was completed, the mixture was stirred for 30 minutes before adding methyl iodide (6 ml) dropwise. The reaction mixture was stirred at room temperature for one hour, water (160 ml) was added and the mixture was extracted with diethyl ether. The organic layer was washed with water and the solvent was removed by evaporation. Purification of the residue by flash chromatography using dichloromethane/ethyl acetate (9.8:0.2) as eluent gave 6-chloro-4-methyl-4,5-dihydro-1,4-benzothiazepin-3(2H)-one. Yield 3.8 g (m.p. 122°-125° C.).

Workup

  1. additionAfter the addition
  2. stirringThe reaction mixture was stirred at room temperature for one hour
  3. extractionthe mixture was extracted with diethyl ether
  4. washThe organic layer was washed with water
  5. customthe solvent was removed by evaporation
  6. customPurification of the residue by flash chromatography

Sources & evidence

ORD record
ord-2669757240da4b83b7420292c4149f16
Source dataset
uspto-grants-1996_12
Patent number
US05580866

Reaction notes

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