Thionyl Chloride → HCID 13140214, compound

HRID 1189584Notes

Reaction equation

HRID 1189584 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([S:7]([C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12](O)=[O:13])(=[O:9])=[O:8])[CH2:3][CH2:2]1.S(Cl)([Cl:21])=O.C[O-].[Na+]>ClCCl.CO>[O:1]1[CH2:6][CH2:5][N:4]([S:7]([C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12]([Cl:21])=[O:13])(=[O:9])=[O:8])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 10942334Sodium MethoxideHCID 131402072-(Morpholine-4-sulfonyl)benzoic acid

Product 1

HCID 13140214HCID 13140214, compoundYield 113.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a slurry of 2-(morpholinosulfonyl)benzoic acid (327 mg, 1.21 mmol) in dichloromethane (11 mL) was added thionyl chloride (0.220 mL, 3.01 mmol). The reaction was heated at 60° C. for 1 hour, after which LCMS analysis (sodium methoxide solution, 25% in methanol) revealed reaction completion. The reaction was concentrated to afford 2-(morpholinosulfonyl)benzoyl chloride (0.397 g, 1.37 mmol) as a viscous yellow residue and this was used in the next step without further purification.

Workup

  1. customreaction completion
  2. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-fd60846647054ad18eb2d58bcbe80704
Source dataset
uspto-grants-2014_03
Patent number
US08674115B2

Reaction notes

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