Oxalyl chloride → HCID 87955231, compound

HRID 2186760Notes

Reaction equation

HRID 2186760 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[CH2:7]([O:9][C:10]1C=[CH:17][C:16]([S:19]([N:22]2[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]2)(=[O:21])=[O:20])=[CH:15][C:11]=1C(O)=O)[CH3:8]>CN(C)C=O.ClCCl>[ClH:4].[CH2:7]([O:9][C:10]1[CH:11]=[CH:15][C:16]([S:19]([N:22]2[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]2)(=[O:21])=[O:20])=[CH:17][C:1]=1[C:2]([Cl:4])=[O:3])[CH3:8]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 121348652-Ethoxy-5-(4-methylpiperazine-1-sulfonyl)benzoic acid

Product 1

HCID 87955231HCID 87955231, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (11.7 ml, 134 mmol) was added dropwise to an ice cold suspension of 2-ethoxy-5-(4-methylpiperazin-1-ylsulphonyl)benzoic acid (EP 812845 A1) (20.0 g, 60.9 mmol) and dimethylformamide (2 drops) in dichloromethane (200 ml) over 15 minutes, and the reaction mixture stirred at room temperature for 18 hours. The mixture was concentrated under reduced pressure, the residue triturated with ether then ethyl acetate and dried at 40° C. for 16 hours, to afford the title compound, (19.6 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue triturated with ether
  3. dry with materialethyl acetate and dried at 40° C. for 16 hours

Sources & evidence

ORD record
ord-87308cba657645fdbe8c21f0f9bc9a46
Source dataset
uspto-grants-2002_06
Patent number
US06407114B1

Reaction notes

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