Water → 2-(2-Allyloxyphenyl)-4-amino-5-nitrosopyrimid-6-one

HRID 1288271Notes

Reaction equation

HRID 1288271 reaction equation
Cl.[CH2:2]([O:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([NH2:10])=[NH:9])[CH:3]=[CH2:4].[Na].[N:16](=[C:18]([C:24]#[N:25])[C:19](OCC)=[O:20])[OH:17].O>CO.C(O)(=O)C>[CH2:2]([O:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]1[NH:10][C:19](=[O:20])[C:18]([N:16]=[O:17])=[C:24]([NH2:25])[N:9]=1)[CH:3]=[CH2:4]

Participants

7

Reactant 4

HCID 962WaterHCID 5360545SodiumHCID 6399078Ethyl 2-cyano-2-(hydroxyimino)acetateHCID 22462384HCID 22462384, compound

Product 1

HCID 1363546152-(2-Allyloxyphenyl)-4-amino-5-nitrosopyrimid-6-oneYield 55.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

2-Allyloxybenzamidine hydrochloride (10.2 g.) was added to a solution of sodium (4.6 g.) in anhydrous methanol (200 ml.) with stirring, followed by ethyl α-oximinocyanoacetate (7.6 g.), and the mixture was stirred under reflux for 6 hours. The hot mixture was poured into water (500 ml.) and acidified with glacial acetic acid. The blue solid was filtered off, washed with water and recrystallised from 50% aqueous acetic acid to give 2-(2-allyloxyphenyl)-4-amino-5-nitrosopyrimid-6-one (7.3 g.), m.p. 217°-220° C.

Workup

  1. stirringthe mixture was stirred
  2. temperatureunder reflux for 6 hours
  3. filtrationThe blue solid was filtered off
  4. washwashed with water
  5. customrecrystallised from 50% aqueous acetic acid

Sources & evidence

ORD record
ord-b1c2585a22d04eddb25559fb155bd831
Source dataset
uspto-grants-1976_10
Patent number
US03987160

Reaction notes

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