N-bromobutanimide → HCID 20195167, compound

HRID 652993Notes

Reaction equation

HRID 652993 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[C:9]([O:11][CH:12]([CH3:14])[CH3:13])[N:8]=[C:7]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[N:6]=1)([CH3:3])[CH3:2].[Br:22]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[C:18]1([CH3:21])[CH:19]=[CH:20][C:15]([C:7]2[N:8]=[C:9]([O:11][CH:12]([CH3:14])[CH3:13])[C:10]([Br:22])=[C:5]([O:4][CH:1]([CH3:2])[CH3:3])[N:6]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 20195166HCID 20195166, compound

Product 1

HCID 20195167HCID 20195167, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

111.7 g of 4,6-diisopropoxy-2-p-tolylpyrimidine and 450 ml of carbon tetrachloride are heated to 70°-75° C. To the resultant solution is added 0.5 g of dibenzoyl peroxide, followed by the addition, over 45 minutes, of a mixture of 1 g of azoisobutyronitrile and 70.8 g of N-bromosuccinimide. The mixture is refluxed for 2 hours to bring the reaction to completion. The precipitated succinimide is then filtered off and excess carbon tetrachloride is removed by distillation, affording 141 g of the title compound with a melting point of 74°-75° C. after purification with methanol.

Workup

  1. temperatureThe mixture is refluxed for 2 hours
  2. customthe reaction to completion
  3. filtrationThe precipitated succinimide is then filtered off
  4. customexcess carbon tetrachloride is removed by distillation

Sources & evidence

ORD record
ord-bdfadca8c3cc435da398981753f63810
Source dataset
uspto-grants-1987_06
Patent number
US04674229

Reaction notes

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