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

HRID 1828141Notes

Reaction equation

HRID 1828141 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-ce7445dc67ae4c7981781957244ef955
Source dataset
uspto-grants-2006_06
Patent number
US07056926B2

Reaction notes

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