Methanol → HCID 54045171, compound

HRID 1287702Notes

Reaction equation

HRID 1287702 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:16][OH:17])=[C:6]([CH:15]=1)[CH:7]([OH:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:18][N:19]=[C:20]=[O:21].[N:22]1[CH:27]=CC=C[CH:23]=1.C[OH:29]>>[CH3:18][NH:19][C:20]([O:14][CH:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:6]1[CH:15]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[CH2:16][O:17][C:23](=[O:29])[NH:22][CH3:27])=[O:21]

Participants

5

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 12228Methyl IsocyanateHCID 12241058HCID 12241058, compound

Product 1

HCID 54045171HCID 54045171, compound

Procedure

In a Parr bomb, 2 g. of the compound of Example 1 is heated for 7 hours at 80°-90° C. with 2 g. of methyl isocyanate and 6 ml. of pyridine. After cooling, the reaction mixture is boiled in methanol for 5 minutes and the solvent is distilled off. The crude residue is triturated with acidic water, and after decantation is dissolved in anhydrous ethyl ether. Concentration of the ether solution gives a product that after crystallization from diisopropyl ether melts at 128°-131° C. Yield 2 g.

Workup

  1. temperatureAfter cooling
  2. distillationthe solvent is distilled off
  3. customThe crude residue is triturated with acidic water
  4. dissolutionafter decantation is dissolved in anhydrous ethyl ether
  5. customConcentration of the ether solution gives a product that
  6. customafter crystallization from diisopropyl ether melts at 128°-131° C

Sources & evidence

ORD record
ord-82e9af0e8e0a48539875c1eabc334627
Source dataset
uspto-grants-1976_10
Patent number
US03985811

Reaction notes

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