N-bromobutanimide → HCID 19375762, compound

HRID 2211379Notes

Reaction equation

HRID 2211379 reaction equation
[CH3:1][C:2]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:14]=[CH:13][C:12]=1[CH2:25][CH3:26])[C:3]#[N:4].[Br:32]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH3:1][C:2]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[C:15]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:14]([Br:32])=[CH:13][C:12]=1[CH2:25][CH3:26])[C:3]#[N:4]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 19375761HCID 19375761, compound

Product 1

HCID 19375762HCID 19375762, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2-Methyl-2-n-pentyl-7-(2-ethyl-5-benzyloxyphenoxy)heptanenitrile and 1.1 equivalents of N-bromosuccinimide in carbon tetrachloride were stirred 1.5 hours, washed with aqueous sodium thiosulfate, washed with saturated sodium chloride, dried over sodium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel eluting with hexane/ethyl ether providing the desired title intermediate in 60% yield, as an oil, NMR.

Workup

  1. washwashed with aqueous sodium thiosulfate
  2. washwashed with saturated sodium chloride
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica gel eluting with hexane/ethyl ether providing the desired title intermediate in 60% yield

Sources & evidence

ORD record
ord-a05740a0074f4291b9645a599ad229f0
Source dataset
uspto-grants-1995_10
Patent number
US05462954

Reaction notes

Loading…