1,2-Dichlorobenzene → HCID 20471877, compound

HRID 1388194Notes

Reaction equation

HRID 1388194 reaction equation
C([NH:5][S:6]([C:9]1[S:10][C:11]([CH3:17])=[CH:12][C:13]=1[C:14]([OH:16])=[O:15])(=[O:8])=[O:7])(C)(C)C.ClC1C=CC=CC=1Cl.[OH-].[Na+]>CCOCC>[CH3:17][C:11]1[S:10][C:9]([S:6](=[O:8])(=[O:7])[NH2:5])=[C:13]([C:14]([OH:16])=[O:15])[CH:12]=1

Participants

5

Reactant 3

HCID 72391,2-DichlorobenzeneHCID 14798Sodium HydroxideHCID 23331879HCID 23331879, compound

Product 1

HCID 20471877HCID 20471877, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 5.0 gm (18 millimols) of 2-(N-tert. butyl)sulfamoyl-5-methyl-thiophene-3-carboxylic acid and 20 ml of o-dichloro-benzene was heated, while stirring, for 4 hours at 140° C. After cooling, the reaction mixture was taken up in a mixture of ether and the equivalent amount of dilute aqueous sodium hydroxide. After separation of the ether phase, the aqueous phase was acidified with hydrochloric acid, and the precipitated material was suction-filtered off. The filter cake was recrystallized from ethyl acetate/cyclohexane, yielding 3.3 gm (83% of theory) of 5-methyl-2-sulfamoylthiophene-3-carboxylic acid.

Workup

  1. temperaturewas heated
  2. temperatureAfter cooling
  3. customAfter separation of the ether phase
  4. filtrationthe precipitated material was suction-filtered off
  5. customThe filter cake was recrystallized from ethyl acetate/cyclohexane

Sources & evidence

ORD record
ord-3306a9c7fe554a2ca74fc2ffe7ce5851
Source dataset
uspto-grants-1984_02
Patent number
US04430355

Reaction notes

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