Benzoyl Peroxide → HCID 67958922, compound

HRID 707651Notes

Reaction equation

HRID 707651 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][O:10][N:9]=2)=[CH:4][N:3]=1.[Br:13]NC(=O)CCC(N)=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[CH:12]=[CH:11][O:10][N:9]=2)=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 9834204N-BromosuccinamideHCID 67958918HCID 67958918, compound

Product 1

HCID 67958922HCID 67958922, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 2-methyl-5-isoxazol-3-yl-pyrimidine (30 gm), N-bromosuccinamide (49.8 gm), and 98% benzoyl peroxide (13.54 gm) in carbon tetrachloride (1200 ml) was heated to 75° C. temperature. The reaction mixture was stirred at 75° C. for 24 h. The reaction mixture was filtered under suction at 25° C. to 35° C. temperature. The solid was washed with carbon tetrachloride (400 ml). The filtrate was washed with saturated aqueous sodium bicarbonate solution (400 ml×2) and evaporated under vacuum to provide a crude material (52 gm) which upon silica gel column chromatography afforded desired compound in 14 gm quantity (40%), dibromo compound in 16.8 gm and starting material 6.5 gm quantities.

Workup

  1. filtrationThe reaction mixture was filtered under suction at 25° C. to 35° C. temperature
  2. washThe solid was washed with carbon tetrachloride (400 ml)
  3. washThe filtrate was washed with saturated aqueous sodium bicarbonate solution (400 ml×2)
  4. customevaporated under vacuum
  5. customto provide a crude material (52 gm) which upon silica gel column chromatography

Sources & evidence

ORD record
ord-f603d851cc774fba8d30703909856d52
Source dataset
uspto-grants-2015_11
Patent number
US09175031B2

Reaction notes

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