Thionyl Chloride → 5-Methoxycarbonyl-2-thiophenecarboxylic acid hydrazide

HRID 1881537Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]([C:10]([OH:12])=O)=[CH:7][CH:6]=1)=[O:4].S(Cl)(Cl)=O.O.[NH2:18][NH2:19]>>[NH:18]([C:10]([C:8]1[S:9][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=1)=[O:12])[NH2:19]

Participants

Reactant 3

HCID 24386Thionyl Chloride

HCID 24654Hydrazine hydrate (1:1)

HCID 8183525-(Methoxycarbonyl)thiophene-2-carboxylic acid

Product 1

HCID 148719615-Methoxycarbonyl-2-thiophenecarboxylic acid hydrazideYield 72%

Procedure

The known procedure disclosed in the literature (J. Heterocyclic Chem., 28, 17, (1991).) was followed using 5-methoxycarbonyl-2-thiophenecarboxylic acid synthesized in Reference Synthetic Example 38, thionyl chloride and hydrazine monohydrate to give 144 mg of the desired product as a white solid (yield 72%).

Sources & evidence

ORD record: ord-ec363db9da67441186960927654e0274
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318796B2

Reaction notes

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