Dimethylformamide → 2-Methoxy-5-Phenoxysulfonylbenzoyl chloride

HRID 1683185Notes

Reaction equation

HRID 1683185 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([S:12]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:14])=[O:13])=[CH:8][C:4]=1[C:5](O)=[O:6].C(Cl)(=O)C([Cl:25])=O.CN(C=O)C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([S:12]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:14])=[O:13])=[CH:8][C:4]=1[C:5]([Cl:25])=[O:6]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 190429722-Methoxy-5-phenoxysulfonylbenzoic acid

Product 1

HCID 190429762-Methoxy-5-Phenoxysulfonylbenzoyl chlorideYield 95.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 2-methoxy-5-phenoxysulfonylbenzoic acid (4.0 g, 13 mmol) in dry toluene (100 mL) was added oxalyl chloride (2.3 mL, 26 mmol) at room temperature. A drop of DMF was added and the mixture stirred at room temperature for 2 h. The mixture was evaporated in vacuo and the residue triturated with 1:1 toluene/hexane to give the title compound as a solid (4.04 g).

Workup

  1. customThe mixture was evaporated in vacuo
  2. customthe residue triturated with 1:1 toluene/hexane

Sources & evidence

ORD record
ord-03d0dcd7d19346b0b9a91f6ad15723b8
Source dataset
uspto-grants-1997_06
Patent number
US05637600

Reaction notes

Loading…