Hydrochloric Acid → 5-(3,4-Dichlorobenzyl-carbamoyl)-thiophene-2-carboxylic acid

HRID 1263610Notes

Reaction equation

HRID 1263610 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[S:9][C:10]([C:13](=[O:24])[NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)=[CH:11][CH:12]=1)=[O:7])C.Cl>C(O)C.O>[Cl:23][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][C:19]=1[Cl:22])[CH2:15][NH:14][C:13]([C:10]1[S:9][C:8]([C:6]([OH:7])=[O:5])=[CH:12][CH:11]=1)=[O:24]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 229861535-(3,4-Dichlorobenzyl-carbamoyl)-thiophene-2-carboxylic acid ethyl ester

Product 1

HCID 186171155-(3,4-Dichlorobenzyl-carbamoyl)-thiophene-2-carboxylic acidYield 83%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Aqueous 1M sodium hydroxide (16.3 mL; 16.3 mmole) was added to a stirring solution of (12(a)) (1.17 g; 3.3 mmole) in ethanol (70 mL). The reaction mixture was stirred at ambient temperature for 19 hours, reduced to a small volume, diluted with water and adjusted to pH 2 by addition of 2M hydrochloric acid. The filtered solid was washed with water and dried in vacuo to give 5-(3,4-dichlorobenzyl-carbamoyl)-thiophene-2-carboxylic acid (12(b)) as a white solid (83%).

Workup

  1. washThe filtered solid was washed with water
  2. customdried in vacuo

Sources & evidence

ORD record
ord-9671c972b588418ba150bc73cd025041
Source dataset
uspto-grants-2003_04
Patent number
US06541491B1

Reaction notes

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