Ethyl 2-cyano-2-(hydroxyimino)acetate → 7-AMINO-1-[(4-CHLOROPHENYL)METHYL]-2,3-DIHYDRO-6-NITROSOIMIDAZO-[1,2-a]PYRIMIDIN-5-(1H)-ONE

HRID 1154380Notes

Reaction equation

HRID 1154380 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]2[CH2:14][CH2:13][N:12]=[C:11]2[NH2:15])=[CH:5][CH:4]=1.[N:16](=[C:18]([C:24]#[N:25])[C:19](OCC)=[O:20])[OH:17]>>[NH2:25][C:24]1[N:15]=[C:11]2[N:10]([CH2:9][C:6]3[CH:5]=[CH:4][C:3]([Cl:2])=[CH:8][CH:7]=3)[CH2:14][CH2:13][N:12]2[C:19](=[O:20])[C:18]=1[N:16]=[O:17]

Participants

3

Reactant 2

HCID 6399078Ethyl 2-cyano-2-(hydroxyimino)acetateHCID 202177121-[(4-Chlorophenyl)methyl]-4,5-dihydro-1H-imidazol-2-amine hydrochloride2×

Product 1

HCID 133914207-AMINO-1-[(4-CHLOROPHENYL)METHYL]-2,3-DIHYDRO-6-NITROSOIMIDAZO-[1,2-a]PYRIMIDIN-5-(1H)-ONE

Procedure

The product of Procedure 91 was condensed with ethyl oximinocyanoacetate according to the method described in Procedure 1. The crude product, 1.6 g., from 2.9 g. of the product of Procedure 91, was a blue solid, m.p. 273°-275° d, recrystallized from dimethylformamide, m.p. 290°-291° d.

Workup

  1. customrecrystallized from dimethylformamide, m.p. 290°-291°

Sources & evidence

ORD record
ord-12a122d22e3047fa9138b38c24a72751
Source dataset
uspto-grants-1984_12
Patent number
US04489078

Reaction notes

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