2-Butynedioic acid → HCID 54409709, compound

HRID 867446Notes

Reaction equation

HRID 867446 reaction equation
[C:1]([C:6]([OH:8])=[O:7])#[C:2][C:3](O)=[O:4].[Cl:9][C:10]1[CH:11]=[C:12]([NH:17][C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=2)=[S:19])[CH:13]=[CH:14][C:15]=1[Cl:16]>CO>[O:4]=[C:3]1[C:2](=[CH:1][C:6]([OH:8])=[O:7])[S:19][C:18](=[N:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=2)[N:17]1[C:12]1[CH:13]=[CH:14][C:15]([Cl:16])=[C:10]([Cl:9])[CH:11]=1

Participants

4

Reactant 2

HCID 3712-Butynedioic acidHCID 4763349Thiourea, N,N'-bis(3,4-dichlorophenyl)-

Product 1

HCID 54409709HCID 54409709, compoundYield 29.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of acetylenedicarboxylic acid (6.6 g, 55 mmoles) and N,N'-bis(3,4-dichlorophenyl)thiourea (20.0 g, 55 mmoles) in methanol (400 mls) is stirred at room temperature for 16 hours. The suspended solid is filtered off and rinsed with cold methanol. The solid is then rinsed repeatedly with boiling CH2Cl2 and filtered off. The combined dichloromethane filtrates are concentrated and cooled to afford the crystalline product (7.6 g), mp 221°-222° C.

Workup

  1. filtrationThe suspended solid is filtered off
  2. washrinsed with cold methanol
  3. washThe solid is then rinsed repeatedly with boiling CH2Cl2
  4. filtrationfiltered off
  5. concentrationThe combined dichloromethane filtrates are concentrated
  6. temperaturecooled

Sources & evidence

ORD record
ord-741e5b64d97b43928c176061e68d0c22
Source dataset
uspto-grants-1988_10
Patent number
US04775677

Reaction notes

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