N-bromobutanimide → HCID 19863158, compound

HRID 1164776Notes

Reaction equation

HRID 1164776 reaction equation
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([O:24][C:25]3[CH:30]=[CH:29][C:28]([CH:31]([CH3:36])[C:32]([O:34][CH3:35])=[O:33])=[CH:27][CH:26]=3)=[O:23])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Br:37]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:37][C:31]([C:28]1[CH:29]=[CH:30][C:25]([O:24][C:22]([C:19]2[CH:20]=[CH:21][C:16]([C:13]3[CH:14]=[CH:15][C:10]([O:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:11][CH:12]=3)=[CH:17][CH:18]=2)=[O:23])=[CH:26][CH:27]=1)([CH3:36])[C:32]([O:34][CH3:35])=[O:33]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 19863177HCID 19863177, compound

Product 1

HCID 19863158HCID 19863158, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of MOPPP (see Example 20d; 1.1 mmole) in dry CCl4 (10 ml) with N-bromosuccinimide (1.8 mmole) and a catalytic quantity of azo-isobutyronitril (5 mg) was heated for 24 hours. After cooling, the reaction mixture was purified directly by column chromatography (silica gel eluted with hexane/chloroform). MBOPP was recrystallised from hexane as fine needles (yield 45%; mp 104°-5° C.). The results of IR, 1H-NMR and mass spectroscopy and elemental analysis were consistent with the assigned structure.

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was purified directly by column chromatography (silica gel eluted with hexane/chloroform)
  3. customMBOPP was recrystallised from hexane as fine needles (yield 45%; mp 104°-5° C.)
  4. customThe results of IR, 1H-NMR and mass spectroscopy and elemental analysis

Sources & evidence

ORD record
ord-4ea146d14f3644439f10451daa9e3b95
Source dataset
uspto-grants-1990_03
Patent number
US04906402

Reaction notes

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