2-Methylthiophene → 5-Methylthiophene-2-sulfonamide

HRID 1464125Notes

Reaction equation

[CH3:1][C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.Cl[S:8]([OH:11])(=O)=[O:9].[OH-].[NH4+:13]>>[CH3:1][C:2]1[S:3][C:4]([S:8]([NH2:13])(=[O:11])=[O:9])=[CH:5][CH:6]=1

Participants

Reactant 3

HCID 111262-Methylthiophene

HCID 14923Ammonium Hydroxide

HCID 24638Chlorosulfonic acid

Product 1

HCID 6009305-Methylthiophene-2-sulfonamide

Procedure

The procedure of Example 3 was followed using 2-methylthiophene (8.0 g, 81.6 mmole), chlorosulfonic acid (28.4 g, 245 mmole) and 200 ml concentrated ammonium hydroxide to produce 5-methyl-2-thiophenesulfonamide which was contacted with 3,4-dichlorophenyl isocyanate (2.61 g, 13.8 mmole) and 1N NaOH (14.5 ml) in 10 ml acetone to provide 3.5 g of the named product as a solid.

Sources & evidence

ORD record: ord-67a63ffbed1c4417a75e9f01866150d9
Source dataset: uspto-grants-1994_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05302724

Reaction notes

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