N-bromobutanimide → HCID 14835366, compound

HRID 1198999Notes

Reaction equation

HRID 1198999 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][N:10]=[C:11]3[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:12]=23)=[CH:4][CH:3]=1.[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][CH2:17][C:16]1[C:11]2[C:12](=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=3)[O:9][N:10]=2)[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 14835365HCID 14835365, compound

Product 1

HCID 14835366HCID 14835366, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 6.4 g (0.0222 mole) of (4-bromophenyl)-7-methyl-2,1-benzisoxazole, 4.0 g (0.0225 mole) of N-bromosuccinimide and 0.1 g of dibenzoyl peroxide in 250 ml of carbon tetrachloride was heated at reflux for 3 hr under flood light illumination and an argon atmosphere, and filtered while still hot. The filtrate was washed twice with 200 ml portions of 10% sodium bicarbonate solution and twice with 200 ml portions of water and dried over sodium sulfate. The sodium sulfate was removed by filtration and the filtrate was concentrated under reduced pressure to a solid residue. The solid was recrystallized from 2-propanol to give 5.9 g (73%) of fluffy yellow crystals, m.p. 159°-161° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hr under flood light illumination
  3. filtrationan argon atmosphere, and filtered while still hot
  4. washThe filtrate was washed twice with 200 ml portions of 10% sodium bicarbonate solution and twice with 200 ml portions of water
  5. dry with materialdried over sodium sulfate
  6. customThe sodium sulfate was removed by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure to a solid residue
  8. customThe solid was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-b8ea666f12fa4af894ba19ac97590e2b
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

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