Hydrogen Sulfide → HCID 178477178, compound

HRID 426982Notes

Reaction equation

[C:1]([O:10]CC)(=[O:9])/[CH:2]=[CH:3]/[C:4]([O:6]CC)=O.[C:13]([O:16]C(=O)C)(=O)[CH3:14].[SH2:20]>>[C:13]([SH:20]=[C:4]([OH:6])[CH2:3][CH2:2][C:1]([OH:10])=[O:9])(=[O:16])[CH3:14]

Participants

Reactant 3

HCID 402Hydrogen Sulfide

HCID 7918Acetic Anhydride

HCID 638144Diethyl fumarate

Product 1

HCID 178477178HCID 178477178, compound

Procedure

When the alkene-1,2-dicarboxylic acid compound starting material is an ester, such as diethyl fumarate, the addition of acetic anhydride and hydrogen sulfide proceeds to give the diethyl ester of S-acetylthiosuccinic acid, which on selective deacetylation, suitably by means of aqueous alcoholic ammonia, gives diethyl thiomalate according to this invention, as illustrated in SCHEME 2 below.

Sources & evidence

ORD record: ord-48167159299043e19c0e7d14ca1b36db
Source dataset: uspto-grants-1979_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04172207

Reaction notes

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