Acetic Acid → 4,6-Dichloro-2-(methylthio)-5-pyrimidinecarbaldehyde oxime

HRID 1666061Notes

Reaction equation

HRID 1666061 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]=O)=[C:6]([Cl:10])[N:5]=[C:4]([S:11][CH3:12])[N:3]=1.Cl.[NH2:14][OH:15].C(O)(=O)C>O>[Cl:1][C:2]1[C:7]([CH:8]=[N:14][OH:15])=[C:6]([Cl:10])[N:5]=[C:4]([S:11][CH3:12])[N:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 443297Hydroxyamine hydrochlorideHCID 46140044,6-Dichloro-2-(methylsulfanyl)pyrimidine-5-carbaldehyde

Product 1

HCID 218222514,6-Dichloro-2-(methylthio)-5-pyrimidinecarbaldehyde oxime

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

4,6-Dichloro-2-methylsulfanyl-pyrimidine-5-carbaldehyde (7.34 g, 33.09 mmol), hydroxylamine hydrochloride (2.31 g, 33.33 mmol), acetic acid (49.6 mL), and water (3.3 mL) were mixed, and heated to 60° C. for 2 hours. The reaction mixture was diluted with water and cooled under ice bath. The precipitate was collected and dried (Yield=6.41 g, 82%). MS (m/z): 238 (M+H).

Workup

  1. temperaturecooled under ice bath
  2. customThe precipitate was collected
  3. customdried (Yield=6.41 g, 82%)

Sources & evidence

ORD record
ord-e5fe192e768e40e2b3a0ba9b960a0a66
Source dataset
uspto-grants-2011_10
Patent number
US08044040B2

Reaction notes

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