Sodium Carbonate → HCID 178513397, compound

HRID 1989132Notes

Reaction equation

HRID 1989132 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[N:11]=[C:10]([C:18]#[N:19])[N:9]=2)=[CH:4][CH:3]=1.Cl.[NH2:21][OH:22].C(=O)([O-])[O-].[Na+].[Na+]>O.C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[C:12]([C:14]([F:16])([F:15])[F:17])[N:11]=[C:10]([C:18]([NH:21][OH:22])=[NH:19])[N:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 57468700HCID 57468700, compound

Product 1

HCID 178513397HCID 178513397, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A stirred mixture of 4-(4-chloro-phenyl)-6-trifluoromethyl-pyrimidine-2-carbonitrile (example B.1) (0.5 g, 1.76 mmol), hydroxylamine hydrochloride (0.45 g, 6.48 mol) and sodium carbonate (0.37 g, 3.53 mol) in water (10 mL) and ethanol (10 mL) was heated under reflux conditions for 2 h. The ethanol was removed partly and the mixture stirred at room temperature for 1 h. The precipitate was collected by filtration, washed with water and dried to yield the title compound (0.53 g, 94%) as a light brown solid. MS (ISP) 316.9 [(M+H)+]; mp 243° C.

Workup

  1. temperaturewas heated under reflux conditions for 2 h
  2. customThe ethanol was removed partly
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-fb62b94c017b4942b964b5ce91df744f
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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