Azobisisobutyronitrile → HCID 59594707, compound

HRID 2263371Notes

Reaction equation

HRID 2263371 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH3:21])=[O:5])[CH3:2].ClCC1OC(CCC2C=CC(C(F)(F)F)=CC=2)=NC=1C.FC(F)(F)C1C=CC(C(N)=O)=CC=1.ClC(C(C)=O)C([O-])=O.[Br:63]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>ClC(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[O:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:19])([F:20])[F:18])=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH2:21][Br:63])=[O:5])[CH3:2]

Participants

8

Reactant 6

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 746844-(Trifluoromethyl)benzamideHCID 219495572-ChloroacetoacetateHCID 235631164-Methyl-2-(4-trifluoromethyl-phenyl)-oxazole-5-carboxylic acid ethyl esterHCID 595948035-Chloromethyl-4-methyl-2-[2-(4-trifluoromethyl-phenyl)-ethyl]-oxazole

Product 1

HCID 59594707HCID 59594707, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a refluxing mixture of 21.5 g 4-methyl-2-(4-trifluoromethyl-phenyl)-oxazole-5-carboxylic acid ethyl ester (synthesized according to the method described for 5-chloromethyl-4-methyl-2-[2-(4-trifluoromethyl-phenyl)-ethyl]-oxazole from 4-trifluoromethyl-benzamide and 2-chloroacetoacetate) in 180 ml tetrachloro-methane were added portionwise a mixture of 15.4 g N-bromosuccinimide and 4.73 g 2,2′-azobis(2-methylpropionitrile). The reaction mixture was heated under reflux for five hours. The cooled reaction mixture was filtered over a celite pad, the filtrate was evaporated in vacuo and the resulting residue was purified by chromatography on silica gel with the eluent petroleum benzene:dichloromethane=7:3 to provide 18.5 g 4-bromomethyl-2-(4-trifluoromethyl-phenyl)-oxazole-5-carboxylic acid ethyl ester.

Workup

  1. customsynthesized
  2. additionwere added portionwise
  3. temperatureThe reaction mixture was heated
  4. temperatureunder reflux for five hours
  5. customThe cooled reaction mixture
  6. filtrationwas filtered over a celite pad
  7. customthe filtrate was evaporated in vacuo
  8. customthe resulting residue was purified by chromatography on silica gel with the eluent petroleum benzene

Sources & evidence

ORD record
ord-68a32c2e10b44bbebb0d03ea260cf46b
Source dataset
uspto-grants-2010_12
Patent number
US07851493B2

Reaction notes

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