N-bromobutanimide → HCID 13557216, compound

HRID 1583475Notes

Reaction equation

HRID 1583475 reaction equation
[CH3:1][O:2][C:3](=[O:13])[NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([Cl:12])[CH:6]=1.[Br:14]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:13])[NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][Br:14])=[C:7]([Cl:12])[CH:6]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 140888Methyl 3-chloro-4-methylcarbanilate

Product 1

HCID 13557216HCID 13557216, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirred solution of 10.9 grams (0.055 mole) of methyl(3-chloro-4-methylphenyl)carbamate in 110 ml of carbon tetrachloride, under an argon atmosphere, was added 9.7 grams (0.055 mole) of N-bromosuccinimide. The reaction mixture was irradiated with a 250 watt brooder lamp, placed at such a distance as to cause a gentle reflux. The reflux was continued for 20 hours. The reaction mixture was cooled and a solid collected by filtration. The solid was slurried with water and the insoluble material collected by filtration. The filter cake was dried to give 8.5 grams of methyl(4-bromomethyl-3-chlorophenyl)carbamate; m.p. 128°-131° C.

Workup

  1. customThe reaction mixture was irradiated with a 250 watt brooder lamp
  2. temperatureThe reaction mixture was cooled
  3. filtrationa solid collected by filtration
  4. filtrationthe insoluble material collected by filtration
  5. customThe filter cake was dried

Sources & evidence

ORD record
ord-af473935b1d14c9289bd9efab18be66b
Source dataset
uspto-grants-1985_11
Patent number
US04552585

Reaction notes

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