Butyl bromide → 1-Butylazonan-2-one

HRID 2295270Notes

Reaction equation

HRID 2295270 reaction equation
[H-].[Na+].[NH:3]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:12].Br[CH2:14][CH2:15][CH2:16][CH3:17]>>[CH2:14]([N:3]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:12])[CH2:15][CH2:16][CH3:17]

Participants

4

Reactant 3

HCID 8002Butyl bromideHCID 13632Octahydro-2H-azonin-2-oneHCID 24758Sodium hydride2×

Product 1

HCID 128332651-Butylazonan-2-oneYield 74.1%

Procedure

Following example 10, 16.32 g of 50% sodium hydride-mineral oil dispersion (8.16 g NaH, 0.34 M), 40 g (0.283 M) of azacyclononan-2-one and 43 g (0.311 M) of 1-bromobutane was refluxed for 22 hours. The reaction mixture was diluted with benzene-tolune and was extracted with water. The organic phase was separated, dried and concentrated to a yellow oil. Distillation afforded 41.4 g (74%) of product; b.p. 166°-170°/0.2 mm.

Workup

  1. temperaturewas refluxed for 22 hours
  2. extractionwas extracted with water
  3. customThe organic phase was separated
  4. customdried
  5. concentrationconcentrated to a yellow oil
  6. distillationDistillation

Sources & evidence

ORD record
ord-75ad326e586f45308967512108aab019
Source dataset
uspto-grants-1984_01
Patent number
US04424210

Reaction notes

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