Water → HCID 12878972, compound

HRID 444395Notes

Reaction equation

HRID 444395 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][CH:18]=[CH:17][CH:16]=1.[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1.O>C(N(CC)CC)C>[C:15]1([CH:4]2[CH:3]([CH2:2][O:1][S:27]([C:24]3[CH:25]=[CH:26][C:21]([CH3:31])=[CH:22][CH:23]=3)(=[O:29])=[O:28])[C:9](=[O:10])[NH:8][C:7]3[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=3[S:5]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 128789492,3-dihydro-3-hydroxymethyl-2-phenyl-1,5-benzothiazepin-4(5H)-one

Product 1

HCID 12878972HCID 12878972, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

5.7 g of 2,3-dihydro-3-hydroxymethyl-2-phenyl-1,5-benzothiazepin-4(5H)-one prepared as described in Reference Example 1 was dissolved in 20 ml of triethylamine. 3.8 g of p-toluenesulfonyl chloride was added to the solution while stirring 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 a mixture of dichloromethane-n-hexane to obtain 8 g of 2,3-dihydro-2-phenyl-3-[(p-toluenesulfonyloxy)methyl]-1,5-benzothiazepin-4(5H)-one as colorless prisms having a melting point of 215° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. customthe precipitated crystals were separated by filtration
  3. customrecrystallized from a mixture of dichloromethane-n-hexane

Sources & evidence

ORD record
ord-6e4565129c6a4c57ac5746bc04c37538
Source dataset
uspto-grants-1981_04
Patent number
US04264497

Reaction notes

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