N-bromobutanimide → HCID 20514104, compound

HRID 1902884Notes

Reaction equation

HRID 1902884 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11]1[CH:16]=[C:15]([CH3:17])[N:14]=[C:13]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)[N:12]=1>ClC(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][CH2:24][C:21]1[CH:22]=[CH:23][C:18]([C:13]2[N:12]=[C:11]([O:10][CH3:9])[CH:16]=[C:15]([CH3:17])[N:14]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 205140954-Methoxy-6-methyl-2-(4-methylphenyl)pyrimidine

Product 1

HCID 20514104HCID 20514104, compoundYield 75.1%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 9.4 g of N-bromosuccinimide and 0.2 g of azoisobutyronitrile is added in portions at 70° C. and in the course of 30 minutes to a solution of 10.7 g of 4-methoxy-6-methyl-2-p-tolylpyrimidine and 0.2 g of dibenzoyl peroxide in 100 ml of anhydrous tetrachloromethane. The mixture is then kept for 2 hours at reflux temperature. After cooling, the succinimide is filtered with suction and the filter cake is washed with 200 ml of tetrachloromethane and the filtrate is concentrated. Recrystallisation from n-hexane affords 11 g (75% of theory) of 2-(4-bromomethylphenyl)-4-methoxy-6-methylpyrimidine with a melting point of 98°-99° C.

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. filtrationthe succinimide is filtered with suction
  4. washthe filter cake is washed with 200 ml of tetrachloromethane
  5. concentrationthe filtrate is concentrated
  6. customRecrystallisation from n-hexane

Sources & evidence

ORD record
ord-2f02c1f727054850a10c993fb209e740
Source dataset
uspto-grants-1982_12
Patent number
US04366189

Reaction notes

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