2-Butynedioic acid → [4-Oxo-3-(3,4,5-trimethoxyphenyl)-2-[(3,4,5-trimethoxyphenyl)imino]-5-thiazolidinylidene]acetic acid

HRID 867435Notes

Reaction equation

HRID 867435 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:13][C:14]([NH:16][C:17]2[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=2)=[S:15])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[C:29]([C:34](O)=[O:35])#[C:30][C:31]([OH:33])=[O:32]>>[O:35]=[C:34]1[C:29](=[CH:30][C:31]([OH:33])=[O:32])[S:15][C:14](=[N:13][C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=2)[N:16]1[C:17]1[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=1

Participants

3

Reactant 2

HCID 3712-Butynedioic acidHCID 17312812N,N'-bis(3,4,5-trimethoxyphenyl)thiourea

Product 1

HCID 53942914[4-Oxo-3-(3,4,5-trimethoxyphenyl)-2-[(3,4,5-trimethoxyphenyl)imino]-5-thiazolidinylidene]acetic acidYield 57.1%

Procedure

Prepared by the method described in Example 1 from N,N'-bis(3,4,5-trimethoxyphenyl)thiourea (26.8 g, 66 mmoles) and acetylenedicarboxylic acid (9.8 g, 86 mmoles). Recrystallization from ethanol gave the product (19 g), mp 250°-252° C.

Workup

  1. customPrepared by the method
  2. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-4de4dc64f39d40899dd594cad10ead30
Source dataset
uspto-grants-1988_10
Patent number
US04775677

Reaction notes

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