N-bromobutanimide → HCID 14835349, compound

HRID 1198983Notes

Reaction equation

HRID 1198983 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]2[C:7]([CH:17]=1)=[C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[O:9][N:10]=2)[CH3:2].[Br:18]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:18][CH:1]([C:3]1[CH:4]=[CH:5][C:6]2[C:7]([CH:17]=1)=[C:8]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[O:9][N:10]=2)[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 14835348HCID 14835348, compound

Product 1

HCID 14835349HCID 14835349, compoundYield 105.5%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 15.4 g (0.069 mole) of 5-ethyl-3-phenyl-2,1-benzisoxazole, 12.4 g (0.0697 mole) of N-bromosuccinimide and 0.3 g of dibenzoyl peroxide in 300 ml of carbon tetrachloride was heated at reflux under floodlight illumination and an argon atmosphere for one hr and then filtered while still hot. The filtrate was concentrated under reduced pressure to give 22.0 g of a semi-solid residue (NMR indicated 80% product). A sample of this semi-solid was triturated with 3 ml of methylene chloride and filtered. The solid filter cake was recrystallized from ethyl ether to give yellow solid, m.p. 118°-119° C. (with decomposition).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under floodlight illumination
  3. filtrationfiltered while still hot
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e8954565c9d9423f885d487f2987bf29
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

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