Potassium Hydroxide → Benzyl 4-(5-hydroxypyrazin-2-yl)phenylcarbamate

HRID 542445Notes

Reaction equation

HRID 542445 reaction equation
O[N:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:3](=[O:12])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl[C:20]1[CH:25]=[N:24][CH:23]=[CH:22][N:21]=1.[OH-:26].[K+]>C(O)(=O)C>[CH2:5]([O:4][C:3]([NH:2][C:13]1[CH:18]=[CH:17][C:16]([C:23]2[N:24]=[CH:25][C:20](=[O:26])[NH:21][CH:22]=2)=[CH:15][CH:14]=1)=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 73277ChloropyrazineHCID 12358018benzyl N-hydroxy-N-phenylcarbamate

Product 1

HCID 12358023Benzyl 4-(5-hydroxypyrazin-2-yl)phenylcarbamate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of benzyl N-hydroxy-N-phenylcarbamate (8.0 g) in ethanolic potassium hydroxide (0.27N; 120 ml) was treated with chloropyrazine (4.18 g) and molecular sieve (0.5 g). The mixture was stirred for 2 hours at room temperature and then allowed to stand for 4 days. Evaporation of the reaction mixture under reduced pressure gave an orange residue which was suspended in dilute acetic acid, filtered off, and heated in hot 1-propanol (about 200 ml). On cooling, the resulting solution gave a golden precipitate of 5-(4-benzyloxycarbonylaminophenyl)-2(1H)-pyrazinone m.p. 240°-4° C.

Workup

  1. waitto stand for 4 days
  2. customEvaporation of the reaction mixture under reduced pressure
  3. customgave an orange residue which
  4. filtrationfiltered off
  5. temperatureheated in hot 1-propanol (about 200 ml)
  6. temperatureOn cooling

Sources & evidence

ORD record
ord-c7917aed8aa442dfa691456eb0e6b1b4
Source dataset
uspto-grants-1987_04
Patent number
US04657906

Reaction notes

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