Water → HCID 67133248, compound

HRID 1295608Notes

Reaction equation

HRID 1295608 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:12]C=O)([CH3:11])[CH3:10])=[C:4]([C:15]([F:18])([F:17])[F:16])[CH:3]=1.[OH-].[K+].O>C(O)CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH2:12])([CH3:10])[CH3:11])=[C:4]([C:15]([F:16])([F:17])[F:18])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 86600684HCID 86600684, compound

Product 1

HCID 67133248HCID 67133248, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

5.70 g (20 mmol) N-[2-(4-chloro-2-trifluoromethyl-phenyl)-1,1-dimethyl-ethyl]-formamide and 3.00 g potassium hydroxide are stirred overnight at 140° C. in 20 mL ethyleneglycol. The reaction mixture is combined with water and repeatedly extracted with dichloromethane. The combined organic phases are washed with water, dried with sodium sulphate and evaporated down. The residue is filtered through a short column containing silica gel (eluant: dichloromethane/methanol/ammonia=9:1:0.1).

Workup

  1. extractionrepeatedly extracted with dichloromethane
  2. washThe combined organic phases are washed with water
  3. dry with materialdried with sodium sulphate
  4. customevaporated down
  5. filtrationThe residue is filtered through a short column
  6. additioncontaining silica gel (eluant: dichloromethane/methanol/ammonia=9:1:0.1)

Sources & evidence

ORD record
ord-295dba8bf32b47338853bc37a8c2b8d7
Source dataset
uspto-grants-2007_07
Patent number
US07244728B2

Reaction notes

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