Hydrochloric Acid → HCID 22219475, compound

HRID 1793952Notes

Reaction equation

HRID 1793952 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:32]C)=[C:7]([S:9]([NH:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH:21]([CH3:23])[CH3:22])=[CH:17][C:16]=2[NH:24][C:25](=[O:31])[C:26]([O:28]CC)=[O:27])(=[O:11])=[O:10])[CH:8]=1)#[N:2].[Cl-].[Li+].Cl>CN(C)C=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:32])=[C:7]([S:9]([NH:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH:21]([CH3:23])[CH3:22])=[CH:17][C:16]=2[NH:24][C:25](=[O:31])[C:26]([OH:28])=[O:27])(=[O:10])=[O:11])[CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 433294Lithium ChlorideHCID 22219519HCID 22219519, compound

Product 1

HCID 22219475HCID 22219475, compoundYield 103.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 0.21 g of ethyl N-[2-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-5-isopropylphenyl]oxalamate in 3 mL of N,N-dimethylformamide was added 56 mg of lithium chloride, and the mixture was stirred at 140° C. for 4 hours. To the reaction mixture was added 1 mol/L hydrochloric acid, and the mixture was extracted with ethyl acetate. After the organic layer was dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure to give 0.198 g of N-[2-[2-(5-cyano-2-hydroxybenzenesulfonylamino)ethyl]-5-isopropylphenyl]oxalamic acid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ab127f38800d49eeb52cfcb36dd55eca
Source dataset
uspto-grants-2006_04
Patent number
US07022689B2

Reaction notes

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