Methanol → HCID 178470201, compound

HRID 1878070Notes

Reaction equation

HRID 1878070 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][C:6]1[CH:7]=[N:8][C:9]([C:12](=[N:14]O)[NH2:13])=[CH:10][CH:11]=1)=[O:4].[CH2:16]([O:18][C:19]([C:21]#[C:22][C:23]([O:25]CC)=O)=[O:20])[CH3:17].C[OH:29]>>[Cl:1][CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:14]=[C:21]([C:19]([O:18][CH2:16][CH3:17])=[O:20])[C:22]([OH:29])=[C:23]([OH:25])[N:13]=2)=[N:8][CH:7]=1)=[O:4]

Participants

4

Reactant 3

HCID 887MethanolHCID 69803Diethyl acetylenedicarboxylateHCID 137068883HCID 137068883, compound

Product 1

HCID 178470201HCID 178470201, compound

Conditions

Temperature
142.5 °C

Procedure

A mixture of compound of example 4 (2.0 g, 8.75 mmol) and diethylacetylene dicarboxylate (0.34 g, 2.36 mmol) was stirred in methanol (20 mL) at a temperature in the range of 60-65° C. for 4 hours. Methanol was removed under reduced pressure and xylene (20 mL) was added and the reaction mixture was heated at a temperature in the range of 140-145° C. for 18 hours. A brownish colored solid obtained was removed by filtration, and the reaction mixture was again stirred at the same temperature for 8 hours to obtain the title compound.

Workup

  1. customMethanol was removed under reduced pressure and xylene (20 mL)
  2. additionwas added
  3. customA brownish colored solid obtained
  4. customwas removed by filtration

Sources & evidence

ORD record
ord-be1a7a22faa94c58aeff7339574a5732
Source dataset
uspto-grants-2012_11
Patent number
US08314103B2

Reaction notes

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