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

HRID 38151Notes

Reaction equation

HRID 38151 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-b3092e2b8e834b1691787ce221fd1980
Source dataset
uspto-grants-2013_09
Patent number
US08524721B2

Reaction notes

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