Pyridine → 3-chloromethyl-2,3-dihydro-2-phenyl-1,5-benzothiazepin-4(5H)-one

HRID 444393Notes

Reaction equation

HRID 444393 reaction equation
O[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.N1C=CC=CC=1.S(Cl)([Cl:29])=O>C1C=CC=CC=1>[Cl:29][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

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 128789492,3-dihydro-3-hydroxymethyl-2-phenyl-1,5-benzothiazepin-4(5H)-one

Product 1

HCID 128789533-chloromethyl-2,3-dihydro-2-phenyl-1,5-benzothiazepin-4(5H)-oneYield 84%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

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 and 1.6 g of pyridine were dissolved in 30 ml of benzene, and 3.6 g of thionyl chloride was added to the solution, followed by heating under refluxing for 1 hour. The solvent was then distilled off and water was added to the residue. The precipitated crystals were filtered, washed with methanol and recrystallized from benzene to obtain 5.1 g of 3-chloromethyl-2,3-dihydro-2-phenyl-1,5-benzothiazepin-4(5H)-one as colorless needles having a melting point of 233° C. (with decomposition).

Workup

  1. temperatureby heating
  2. temperatureunder refluxing for 1 hour
  3. distillationThe solvent was then distilled off
  4. additionwater was added to the residue
  5. filtrationThe precipitated crystals were filtered
  6. washwashed with methanol
  7. customrecrystallized from benzene

Sources & evidence

ORD record
ord-6fb22d229bf24350b8254f5d40ec54c0
Source dataset
uspto-grants-1981_04
Patent number
US04264497

Reaction notes

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