Dimethylformamide → HCID 15334440, compound

HRID 1288674Notes

Reaction equation

HRID 1288674 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[C:14]([OH:20])[CH:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[CH:21]1([C:24]([CH2:26]Br)=[O:25])[CH2:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[C:14]([O:20][CH2:26][C:24]([CH:21]3[CH2:23][CH2:22]3)=[O:25])[CH:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 109208412-Bromo-1-cyclopropylethan-1-oneHCID 15334439HCID 15334439, compound

Product 1

HCID 15334440HCID 15334440, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of 1.5 g of 3-chloro-2-(4-cyano-3-hydroxyphenyl)-5-trifluoromethylpyridine, 1.2 g of bromomethyl cyclopropyl ketone, 1.5 g of potassium carbonate and 50 ml of anhydrous dimethylformamide was stirred for 40 hours at 23° C. After addition of 200 ml of water, the mixture was extracted three times with 50 ml of methyl tert-butyl ether each time. The combined organic phases were washed with 50 ml of water, then dried over sodium sulfate and concentrated. The residue which remained was crystallized by triturating with n-hexane. Yield: 1.6 g of white crystals having a melting point of 115°-116° C.

Workup

  1. extractionthe mixture was extracted three times with 50 ml of methyl tert-butyl ether each time
  2. washThe combined organic phases were washed with 50 ml of water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue which remained was crystallized
  6. customby triturating with n-hexane

Sources & evidence

ORD record
ord-7272c5e93a404d9880028bcd843297d9
Source dataset
uspto-grants-1998_05
Patent number
US05747422

Reaction notes

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