2-Butynedioic acid → [3-Pentyl-2-(pentylimino)-4-oxo-5-thiazolidinylidene]acetic acid

HRID 867433Notes

Reaction equation

HRID 867433 reaction equation
[CH2:1]([NH:6][C:7]([NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[S:8])[CH2:2][CH2:3][CH2:4][CH3:5].[C:15]([C:20](O)=[O:21])#[C:16][C:17]([OH:19])=[O:18]>>[CH2:10]([N:9]1[C:20](=[O:21])[C:15](=[CH:16][C:17]([OH:19])=[O:18])[S:8][C:7]1=[N:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:11][CH2:12][CH2:13][CH3:14]

Participants

3

Reactant 2

HCID 3712-Butynedioic acidHCID 10751225N,N'-dipentylthiourea

Product 1

HCID 54079663[3-Pentyl-2-(pentylimino)-4-oxo-5-thiazolidinylidene]acetic acidYield 44%

Procedure

Prepared by the method described in Example 1 from N,N'-dipentylthiourea (31.4 g, 150 mmoles) and acetylenedicarboxylic acid (17.1 g, 150 mmoles). Recrystallization from acetonitrile gave the product (20.6 g), mp 85°-88° C.

Workup

  1. customPrepared by the method
  2. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-5a7e34759ad941ec9e2d25cf28f95ecd
Source dataset
uspto-grants-1988_10
Patent number
US04775677

Reaction notes

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