N-bromobutanimide → HCID 19742092, compound

HRID 2255284Notes

Reaction equation

HRID 2255284 reaction equation
[CH3:1][O:2][N:3]([CH3:19])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)=[O:5].[Br:20]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl.C(#N)N(C)C>[Br:20][CH2:18][C:15]1[CH:16]=[CH:17][C:12]([C:9]2[CH:10]=[CH:11][C:6]([C:4]([N:3]([O:2][CH3:1])[CH3:19])=[O:5])=[CH:7][CH:8]=2)=[CH:13][CH:14]=1

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 19742057HCID 19742057, compound

Product 1

HCID 19742092HCID 19742092, compoundYield 78.3%

Reagents, catalysts & solvents 3

HCID 15112DimethylcyanamideCatalystHCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

4 g of N-methoxy-N-methyl-4'-methyl-4-biphenylcarboxamide, 3.34 g of N-bromosuccinimide and 0.02 g of azaisobutyronitrile in 50 mL of carbon tetrachloride were heated to boiling under reflux for 18 hours. The reaction mixture was diluted with 50 mL of methylene chloride and washed twice with 50 mL of water each time and once with 50 mL of saturated sodium chloride solution. The organic phases were dried over magnesium sulphate and concentrated. The residue was recrystallized from ethyl acetate. There was obtained 4.1 g (78%) of 4'-bromomethyl-N-methoxy-N-methyl-4-biphenylcarboxamide as a solid with a m.p. of 105°-106° C.

Workup

  1. temperatureunder reflux for 18 hours
  2. washwashed twice with 50 mL of water each time
  3. dry with materialThe organic phases were dried over magnesium sulphate
  4. concentrationconcentrated
  5. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-f6e626ce8f5b46819407badde702996c
Source dataset
uspto-grants-1993_08
Patent number
US05239084

Reaction notes

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