Sulfuric Acid → HCID 66919737, compound

HRID 1967560Notes

Reaction equation

HRID 1967560 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[N:8]=[C:7]([C:9](O)([CH3:11])[CH3:10])[CH:6]=[CH:5][N:4]=1.S(=O)(=O)(O)[OH:16].[C:20](#[N:22])[CH3:21]>>[CH3:10][C:9]([NH:22][C:20](=[O:16])[CH3:21])([C:7]1[CH:6]=[CH:5][N:4]=[C:3]([C:2]([F:14])([F:13])[F:1])[N:8]=1)[CH3:11]

Participants

4

Reactant 3

HCID 1118Sulfuric Acid2×HCID 6342Acetonitrile3×HCID 58138255HCID 58138255, compound2×

Product 1

HCID 66919737HCID 66919737, compoundYield 78%

Conditions

Temperature
90 °C

Procedure

Heat a solution of acetonitrile (300 mL) and 2-(2-trifluoromethyl-pyrimidin-4-yl)-propan-2-ol (16.5 g, 80 mmol) to 90° C. In a separate reaction vessel, cool acetonitrile (70 mL) to 0° C. and add sulfuric acid (19.2 mL, 360 mmol) at such a rate that the temperature does not exceed 10° C. Add the cooled sulfuric acid solution to the heated solution of 2-(2-trifluoromethyl-pyrimidin-4-yl)-propan-2-ol and acetonitrile and stir at 90° C. for 60 minutes. Cool to room temperature, concentrate to about ⅓ original volume, and add aqueous 5N NaOH (150 mL). Partition between ethyl acetate and brine then extract the aqueous layer with ethyl acetate (3×). Concentrate under reduced pressure the combined organic layers to yield N-[1-methyl-1-(2-trifluoromethyl-pyrimidin-4-yl)-ethyl]-acetamide (15.4 g, 78%) as a yellow solid. MS (m/z): 248.0 (M+H)+.

Workup

  1. customIn a separate reaction vessel
  2. customdoes not exceed 10° C
  3. temperatureCool to room temperature
  4. concentrationconcentrate to about ⅓ original volume
  5. additionadd aqueous 5N NaOH (150 mL)
  6. customPartition between ethyl acetate and brine
  7. extractionthen extract the aqueous layer with ethyl acetate (3×)
  8. concentrationConcentrate under reduced pressure the combined organic layers

Sources & evidence

ORD record
ord-534ef5c0d4694785924c30c913308231
Source dataset
uspto-grants-2013_04
Patent number
US08420654B2

Reaction notes

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