4-Methylcyclohexanone → Pyrazinamide

HRID 1680202Notes

Reaction equation

HRID 1680202 reaction equation
N[C:2]1[C:3]([C:10]([NH:12]C=NNC(N)=O)=[O:11])=[N:4][C:5](Cl)=[C:6](N)[N:7]=1.CC1CCC(=O)CC1>CN(C)C=O>[N:4]1[CH:5]=[CH:6][N:7]=[CH:2][C:3]=1[C:10]([NH2:12])=[O:11]

Participants

4

Reactant 2

HCID 115254-MethylcyclohexanoneHCID 136335648HCID 136335648, compound

Product 1

HCID 1046Pyrazinamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3,5-diamino-6-chloro-N-[[(aminocarbonyl)amino]iminomethyl]-2-pyrazinecarboxamide (0.5 g., 0.0018 mole) and 4-methylcyclohexanone (0.5 ml.) in dimethylformamide (10 ml.) is heated at 95° C. for 20 hours. The reaction mixture is treated with 20 ml. of 2-propanol, filtered, the filtrate distilled at reduced pressure to a volume of 2 ml. and chromatographed on silica gel to give 3,5-diamino-6-chloro-N-(3',4'-dihydro-6'-hydroxy-4-methylspirocyclohexane]1,4']-1,3,5-triazin-2-yl)-2-pyrazinecarboxamide which melts at 274° C.

Workup

  1. additionThe reaction mixture is treated with 20 ml
  2. filtrationof 2-propanol, filtered
  3. distillationthe filtrate distilled at reduced pressure to a volume of 2 ml
  4. customand chromatographed on silica gel

Sources & evidence

ORD record
ord-709ab9cfb43448e4a59b7d2a49172b6c
Source dataset
uspto-grants-1981_06
Patent number
US04272537

Reaction notes

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