Hexane → 2-(4-methoxyphenyl)-3-chloro-1,5-benzothiazepin-4(5H)-one

HRID 703617Notes

Reaction equation

HRID 703617 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:15](O)[C:14](=[O:17])[NH:13][C:12]3[CH:18]=[CH:19][CH:20]=[CH:21][C:11]=3[S:10]2)=[CH:5][CH:4]=1.S(Cl)([Cl:24])=O.CCCCCC>CCOCC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11]3[CH:21]=[CH:20][CH:19]=[CH:18][C:12]=3[NH:13][C:14](=[O:17])[C:15]=2[Cl:24])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 24386Thionyl ChlorideHCID 27336733-Hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, (2S,3S)-

Product 1

HCID 221508062-(4-methoxyphenyl)-3-chloro-1,5-benzothiazepin-4(5H)-oneYield 66%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Under a nitrogen blanket, a 2.0 g sample of dl-cis-2-(4-methoxyphenyl)-2,3-dihydro-3-hydroxy-1,5-benzothiazepin-4(5H)-one (6.8 mmol) was refluxed neat with 20 mL of thionyl chloride (27.6 mmol) for approximately 2 hours. Then, 50 mL of hexane and about 20 mL of ether were added, and solid product was filtered off. The solid was dried under vacuum to obtain 1.4 g of 2-(4-methoxyphenyl)-3-chloro-1,5-benzothiazepin-4(5H)-one (66 percent yield of theory).

Workup

  1. filtrationsolid product was filtered off
  2. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-581335cfc769495bad670fac2b1ec5c9
Source dataset
uspto-grants-1991_01
Patent number
US04983733

Reaction notes

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