Water → HCID 19850148, compound

HRID 542544Notes

Reaction equation

HRID 542544 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 dimethyformamide (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 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°
  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-b825ac7a5f5944edba3d42fb873878e2
Source dataset
uspto-grants-1987_04
Patent number
US04657929

Reaction notes

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