Dimethylformamide → 5-(4-Isocyanatophenyl)pyrazin-2(1H)-one

HRID 542461Notes

Reaction equation

HRID 542461 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][C:11](=[O:14])[NH:12][CH:13]=2)=[CH:4][CH:3]=1.CN(C)[CH:17]=[O:18]>C(N(CC)CC)C>[N:1]([C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[CH:10][C:11](=[O:14])[NH:12][CH:13]=2)=[CH:6][CH:7]=1)=[C:17]=[O:18]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 123580285-(4-Aminophenyl)pyrazin-2(1H)-one

Product 1

HCID 202086615-(4-Isocyanatophenyl)pyrazin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

5-(4-Aminophenyl)pyrazin-2(1H)-one (1 g) was dissolved in dimethylformamide (20 ml) and triethylamine (1.0 ml). The dark solution was filtered through diatomaceous earth, and then added dropwise to an ice-cooled solution of N,N'-carbonyldiimidazole (3.0 g) in dimethylformamide (20 ml) over 11/2 hours. The mixture was stirred for a further 30 minutes, to form 5-[4-(isocyanato)phenyl]-2(1H)-pyrazinone.

Workup

  1. filtrationThe dark solution was filtered through diatomaceous earth
  2. additionadded dropwise to an ice-
  3. temperaturecooled solution of N,N'-carbonyldiimidazole (3.0 g) in dimethylformamide (20 ml) over 11/2 hours

Sources & evidence

ORD record
ord-16f0ecb43644401c93504e4fcd0559d0
Source dataset
uspto-grants-1987_04
Patent number
US04657906

Reaction notes

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