Sulfuric Acid → HCID 58542527, compound

HRID 1843081Notes

Reaction equation

HRID 1843081 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]([C:10]([F:13])([F:12])[F:11])=[C:4]([C:14]([F:20])([F:19])[C:15]([F:18])([F:17])[F:16])[N:3]=1.S(=O)(=O)(O)[OH:22]>>[CH3:1][C:2]1[N:7]=[C:6]([C:8]([NH2:9])=[O:22])[C:5]([C:10]([F:12])([F:11])[F:13])=[C:4]([C:14]([F:20])([F:19])[C:15]([F:16])([F:17])[F:18])[N:3]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 2848522HCID 2848522, compound

Product 1

HCID 58542527HCID 58542527, compound

Conditions

Temperature
100 °C

Procedure

4.70 g (15.4 mmol) of 2-methyl-6-(pentafluoroethyl)-5-(trifluoromethyl)pyrimidine-4-carbonitrile are dissolved in 80 ml of concentrated sulphuric acid. The reaction mixture is stirred for 12 hours at 100° C. and then added to 300 ml of ice water. The aqueous phase is extracted four times with ethyl acetate. The combined organic phases are dried over sodium sulphate and the solvent is concentrated by evaporation under reduced pressure on a rotary evaporator. Half of the crude product was purified by, means of flash chromatography on silica gel (eluent: cyclohexane/ethyl acetate=1/1). This gives 0.63 g of 2-methyl-6-(pentafluoroethyl)-5-(trifluoromethyl)pyrimidine-4-carboxamide (13%) as a viscous oil.

Workup

  1. extractionThe aqueous phase is extracted four times with ethyl acetate
  2. dry with materialThe combined organic phases are dried over sodium sulphate
  3. concentrationthe solvent is concentrated by evaporation under reduced pressure on a rotary evaporator
  4. customHalf of the crude product was purified by, means of flash chromatography on silica gel (eluent: cyclohexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-664f417fd7ce48baadbce0d8248d2a2e
Source dataset
uspto-grants-2015_02
Patent number
US08946234B2

Reaction notes

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