2-Butynedioic acid → HCID 54401087, compound

Reaction equation

[CH3:1][NH:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([Cl:13])[CH:7]=1)=[S:4].[C:14]([C:19]([OH:21])=[O:20])#[C:15][C:16](O)=[O:17]>>[Cl:13][C:8]1[CH:7]=[C:6]([N:5]=[C:3]2[N:2]([CH3:1])[C:16](=[O:17])[C:15](=[CH:14][C:19]([OH:21])=[O:20])[S:4]2)[CH:11]=[CH:10][C:9]=1[Cl:12]

Participants

Reactant 2

HCID 3712-Butynedioic acid

HCID 28088391-(3,4-dichlorophenyl)-3-methylthiourea

Product 1

HCID 54401087HCID 54401087, compoundYield 64.7%

Procedure

Prepared by the method described in Example 1 from N-methyl-N'-(3,4-dichlorophenyl)thiourea (4.9 g, 21 mmoles) and acetylenedicarboxylic acid (2.6 g, 22 mmoles). Recrystallization from ethyl acetate gave the product (4.5 g), mp 225°-226° C.

Workup

customPrepared by the method
customRecrystallization from ethyl acetate

Sources & evidence

ORD record: ord-6fe99a330e724cf9b9e2ab646af7dd15
Source dataset: uspto-grants-1988_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04775677

Reaction notes

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