Water → 5-(4-benzyloxycarbonylaminophenyl)-3-methyl-2(1H)-pyrazinone

HRID 1249486Notes

Reaction equation

HRID 1249486 reaction equation
[H-].[Na+].O[N:4]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl[C:22]1[C:27]([CH3:28])=[N:26][CH:25]=[CH:24][N:23]=1.[OH2:29]>CN(C)C=O>[CH2:7]([O:6][C:5]([NH:4][C:15]1[CH:20]=[CH:19][C:18]([C:25]2[N:26]=[C:27]([CH3:28])[C:22](=[O:29])[NH:23][CH:24]=2)=[CH:17][CH:16]=1)=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 66769Pyrazine, 2-chloro-3-methyl-HCID 12358018benzyl N-hydroxy-N-phenylcarbamate

Product 1

HCID 138535615-(4-benzyloxycarbonylaminophenyl)-3-methyl-2(1H)-pyrazinone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of sodium hydride (2.1 g, 50% in oil) in dry dimethylformamide (35 ml) with external cooling was added portionwise, benzyl N-hydroxy-N-phenylcarbamate (10.6 g). After 5 minutes a brown solution was obtained to which was added 2-chloro-3-methylpyrazine (5.5 g) and the mixture was allowed to attain room temperature. The solution was poured into water (200 ml) and the aqueous phase decanted from the dark oil. The aqueous solution deposited a yellow solid which was collected and washed with ethanol to give 5-(4-benzyloxycarbonylaminophenyl)-3-methyl-2(1H)-pyrazinone (1.55 g. m.p. 238°-240° C.).

Workup

  1. temperaturewith external cooling
  2. additionwas added portionwise
  3. customAfter 5 minutes a brown solution was obtained to which
  4. customto attain room temperature
  5. customthe aqueous phase decanted from the dark oil
  6. customwas collected
  7. washwashed with ethanol

Sources & evidence

ORD record
ord-d8517f2feb804372937648ed7e174e71
Source dataset
uspto-grants-1986_12
Patent number
US04632924

Reaction notes

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