Water → HCID 13154618, compound

HRID 444394Notes

Reaction equation

HRID 444394 reaction equation
[OH:1][CH2:2][CH:3]1[C:9](=[O:10])[NH:8][C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[S:5][CH:4]1[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1.[CH3:22][S:23](Cl)(=[O:25])=[O:24].O>N1C=CC=CC=1>[CH3:22][S:23]([O:1][CH2:2][CH:3]1[C:9](=[O:10])[NH:8][C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[S:5][CH:4]1[C:15]1[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=1)(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 12878963HCID 12878963, compound

Product 1

HCID 13154618HCID 13154618, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3 g of 2,3-dihydro-3-hydroxymethyl-2-(p-tolyl)-1,5-benzothiazepin-4(5H)-one prepared as described in Reference Example 3 was dissolved in 15 ml of pyridine. 1.3 g of methanesulfonyl chloride was added to the solution and the mixture was stirred at room temperature for 2 hours. Water was added to the reaction mixture and the precipitated crystals were separated by filtration and recrystallized from dichloromethane-n-hexane to obtain 3.3 g of 2,3-dihydro-3-[(methylsulfonyloxy)methyl]-2-(p-tolyl)-1,5-benzothiazepin-4(5H)-one as colorless needles having a melting point of 207° C.

Workup

  1. customthe precipitated crystals were separated by filtration
  2. customrecrystallized from dichloromethane-n-hexane

Sources & evidence

ORD record
ord-f7901b3ac2c943d39fae53eadd6f6a3f
Source dataset
uspto-grants-1981_04
Patent number
US04264497

Reaction notes

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