Lithium Hydroxide → 4-(4-Methylbenzamido)-2-p-tolylthiophene-3-carboxylic acid

HRID 1918219Notes

Reaction equation

HRID 1918219 reaction equation
[CH3:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([NH:8][C:9]2[C:10]([C:21]([O:23]C)=[O:22])=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)[S:12][CH:13]=2)=[O:7])=[CH:4][CH:3]=1.[OH-].[Li+]>O1CCCC1.CO.O.CN(C=O)C>[CH3:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([NH:8][C:9]2[C:10]([C:21]([OH:23])=[O:22])=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)[S:12][CH:13]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67052278Methyl 4-(4-methylbenzamido)-2-p-tolylthiophene-3-carboxylate

Product 1

HCID 670524264-(4-Methylbenzamido)-2-p-tolylthiophene-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

The ester 180 and lithium hydroxide in tetrahydrofuran: methanol:water (3:2:1) is stirred at room temperature for 4 h. The mixture is diluted with DMF and purified by HPLC to provide 181.

Workup

  1. custompurified by HPLC

Sources & evidence

ORD record
ord-df03c282fa984dfc8f8ff7473787c1ef
Source dataset
uspto-grants-2013_12
Patent number
US08618307B2

Reaction notes

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