Water → HCID 19850148, compound

HRID 414391Notes

Reaction equation

HRID 414391 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]([NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].[H-].[Na+].[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]Br.O>CN(C)C=O>[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][N:5]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3](=[O:4])[C:2]([F:14])([F:15])[F:1]

Participants

6

Reactant 4

HCID 962WaterHCID 123681,6-DibromohexaneHCID 24758Sodium hydrideHCID 2788842,2,2-Trifluoro-N-(2-phenylethyl)acetamide

Product 1

HCID 19850148HCID 19850148, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2,2,2-Trifluoro-N-(2-phenylethyl)acetamide (21.7 g., 0.1 mole) in dry dimethylformamide (100 ml) was added dropwise with stirring and under nitrogen to sodium hydride (2.4 g., 0.1 mole, ether washed) in dry dimethylformamide (150 ml). Stirring was continued until a clear solution was obtained and 1,6-dibromohexane (73.2 g., 0.3 moles) was added. The solution was heated at 60° for 3 hr then poured into water and extracted with ether. The extracts were washed well with water and dried and evaporated. Excess dibromohexane was recovered by distillation (b.p. 60°-70°/0.1 mmHg) and the residue was separated on a silica gel column using ether-light petroleum (1:2) as eluant. The major fraction was evaporated to give the title compound as a pale yellow oil (24 g). A sample was distilled to give a colourless viscous liquid, b.p. 146°-152°/0.05 mmHg, (with slight decomposition).

Workup

  1. customwas obtained
  2. temperatureThe solution was heated at 60° for 3 hr
  3. extractionextracted with ether
  4. washThe extracts were washed well with water
  5. customdried
  6. customevaporated
  7. distillationExcess dibromohexane was recovered by distillation (b.p. 60°-70°/0.1 mmHg)
  8. customthe residue was separated on a silica gel column
  9. customThe major fraction was evaporated

Sources & evidence

ORD record
ord-0a7d78fb33c0495e9a27946a9ea2829a
Source dataset
uspto-grants-1988_12
Patent number
US04791216

Reaction notes

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