Lithium Hydroxide → 4-({[(5-Chloro-2-thienyl)sulfonyl]amino}carbonylamino)benzoic acid

HRID 1071736Notes

Reaction equation

HRID 1071736 reaction equation
[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][C:11]([NH:13][C:14]2[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[CH:16][CH:15]=2)=[O:12])(=[O:9])=[O:8])=[CH:4][CH:3]=1.[Li+].[OH-]>CO.C(#N)C>[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][C:11]([NH:13][C:14]2[CH:23]=[CH:22][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=2)=[O:12])(=[O:9])=[O:8])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 22064417Methyl 4-({[(5-chloro-2-thienyl)sulfonyl]amino}carbonylamino)benzoate

Product 1

HCID 220644524-({[(5-Chloro-2-thienyl)sulfonyl]amino}carbonylamino)benzoic acidYield 127.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

To a suspension of methyl 4-({[(5-chloro-2-thienyl)sulfonyl]amino}carbonylamino)benzoate (56 mg, 0.15 mmol) in methanol (1 mL) and acetonitrile (1 mL) was added 1N LiOH (0.16 mL, 0.16 mmol). The resulting solution was stirred at room temp for 21 hr, then an additional 0.32 mL 1N LiOH was added and the reaction was stirred at 40° C. for another 21 hr til complete. Concentration in vacuo gave crude 4-({[(5-chloro-2-thienyl)sulfonyl]amino}carbonylamino)benzoic acid (69 mg). ES-MS (M+H)+=361.

Workup

  1. stirringthe reaction was stirred at 40° C. for another 21 hr til complete
  2. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-ad3566c00117425d9b9b2a360034a85e
Source dataset
uspto-grants-2005_06
Patent number
US06906063B2

Reaction notes

Loading…