Oxalyl chloride → 2-chloro-5-(N-cyclopropylsulfamoyl)benzoyl isocyanate

HRID 59303Notes

Reaction equation

HRID 59303 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11](=[O:17])(=[O:16])[NH:12][CH:13]2[CH2:15][CH2:14]2)=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].C(Cl)(=O)[C:19](Cl)=[O:20]>C(Cl)CCl>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11](=[O:17])(=[O:16])[NH:12][CH:13]2[CH2:14][CH2:15]2)=[CH:7][C:3]=1[C:4]([N:6]=[C:19]=[O:20])=[O:5]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 900201032-chloro-5-(N-cyclopropylsulfamoyl)benzamide

Product 1

HCID 900195252-chloro-5-(N-cyclopropylsulfamoyl)benzoyl isocyanateYield 91.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 2-chloro-5-(N-cyclopropylsulfamoyl)benzamide (1.50 g, 5.46 mmol) in EDC (20 mL) was added oxalyl chloride (0.59 mL, 6.55 mmol). The reaction mass was refluxed for 1-2 h. Excess of solvent was removed under vacuum to afford 1.5 g of desired product.

Workup

  1. temperatureThe reaction mass was refluxed for 1-2 h
  2. customExcess of solvent was removed under vacuum

Sources & evidence

ORD record
ord-5299d67f9739406ead86bf66f81a4157
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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