Thionyl Chloride → HCID 86628747, compound

HRID 2421851Notes

Reaction equation

HRID 2421851 reaction equation
[CH3:1][C:2]1([CH3:25])[S:8][C:7]2[CH:9]=[CH:10][C:11]([C:13](O)=[O:14])=[CH:12][C:6]=2[N:5]([S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:4][CH2:3]1.S(Cl)([Cl:28])=O>ClCCCl>[CH3:1][C:2]1([CH3:25])[S:8][C:7]2[CH:9]=[CH:10][C:11]([C:13]([Cl:28])=[O:14])=[CH:12][C:6]=2[N:5]([S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 57617803HCID 57617803, compound

Product 1

HCID 86628747HCID 86628747, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2,2-dimethyl-5-(phenylsulfonyl)-2,3,4,5-tetrahydrobenzo[b][1,4]-thiazepine-7-carboxylic acid (480 mg, 1.272 mmol) in DCE (20 mL) was added thionyl chloride (2 mL, 27.4 mmol). The reaction was heated to 70° C. and stirred at that temperature for 2 hours. LCMS analysis of the reaction mixture indicated consumption of starting material. The solvent was removed under reduced pressure and 2,2-dimethyl-5-(phenylsulfonyl)-2,3,4,5-tetrahydrobenzo[b][1,4]thiazepine-7-carbonyl chloride (500 mg, 1.263 mmol, 99% yield) was used without further purification.

Workup

  1. customconsumption of starting material

Sources & evidence

ORD record
ord-731a6b36ada24f799fe495dc9433f50f
Source dataset
uspto-grants-2011_06
Patent number
US07960376B2

Reaction notes

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