Acetic Acid → 2-Amino-4,6-dichloro-pyrimidine-5-carbaldehyde oxime

HRID 1356114Notes

Reaction equation

HRID 1356114 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH:9]=O)=[C:4]([Cl:11])[N:3]=1.C(O)(=O)C.Cl.[NH2:17][OH:18]>C(O)C>[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH:9]=[N:17][OH:18])=[C:4]([Cl:11])[N:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2655462-Amino-4,6-dichloropyrimidine-5-carboxaldehydeHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 731656572-Amino-4,6-dichloro-pyrimidine-5-carbaldehyde oximeYield 84.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following the method of Bell et al. (J. Heterocyclic Chem. 1983, 20, 41), to a solution of 29.6 g (154 mmol) 2-amino-4,6-dichloro-pyrimidine-5-carbaldehyde in 31 acetic acid in a 2-necked flask at room temperature was added dropwise with stirring a solution of 11.8 g (170 mmol) hydroxylamine hydrochloride in 2.31 ethanol. Stirring was continued for 3 h at room temperature during which time crystallisation occurred. The crystals were collected by filtration to afford 26.8 g (84%) 2-amino-4,6-dichloro-pyrimidine-5-carbaldehyde oxime as a light yellow crystalline solid. ES-MS m/e (%): 209 ([M{37Cl, 37Cl}-H]−, 20), 207 ([M{37Cl, 35Cl}-H]−, 55), 205 ([M{35Cl, 35Cl}-H]−, 100).

Workup

  1. customwas continued for 3 h at room temperature during which time crystallisation
  2. filtrationThe crystals were collected by filtration

Sources & evidence

ORD record
ord-d1b98c43b1454740855e6267ea4d0e05
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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