Dimethyl acetylenedicarboxylate → HCID 178499652, compound

HRID 987559

Reaction equation

HRID 987559 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]([NH2:12])=[S:11].[C:13]([C:19](OC)=[O:20])#[C:14][C:15]([O:17][CH3:18])=[O:16]>CO>[CH3:18][O:17][C:15](=[O:16])[CH:14]=[C:13]1[S:11][C:10]([NH:9][C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=2[Cl:8])=[N:12][C:19]1=[O:20]

Participants

4

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 722776N-(2,6-Dichlorophenyl)thiourea

Product 1

HCID 178499652HCID 178499652, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

2,6-Dichlorophenylthiourea (3.0 g, 13.6 mmol) was dissolved in 50 mL of dry methanol and dimethyl acetylenedicarboxylate (13.8 mmol, 1.7 mL) was added over a 10-minute period. The mixture was stirred at 25° C. for 40 minutes, then the mixture was heated at 55° C. for 3 hours. The solvent was removed by rotvap, and the crude product was recrystallized from methanol to yield the desired product.

Workup

  1. temperaturethe mixture was heated at 55° C. for 3 hours
  2. customThe solvent was removed by rotvap
  3. customthe crude product was recrystallized from methanol

Sources & evidence

ORD record
ord-47ab7d127d864fd887dbef69ec9c27e4
Source dataset
uspto-grants-2003_10
Patent number
US06632831B2

Linked notes

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