N-bromobutanimide → Phenyl N-Methoxy-N-(2-bromomethylphenyl)carbamate

HRID 362473Notes

Reaction equation

HRID 362473 reaction equation
[CH3:1][O:2][N:3]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])[C:4](=[O:12])[O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Br:20]N1C(=O)CCC1=O>BrN1C(=O)CCC1=O.C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][N:3]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][Br:20])[C:4](=[O:12])[O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 15767250phenyl N-methoxy-N-(2-methylphenyl)carbamate

Product 1

HCID 21191830Phenyl N-Methoxy-N-(2-bromomethylphenyl)carbamateYield 68.6%

Reagents, catalysts & solvents 2

HCID 67184N-bromobutanimideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 324 g (1.3 mol) of phenyl N-methoxy-N-(2-methylphenyl)carbamate (Example 2b), 258 g (1.45 mol) of N-bromosuccinimide and 1 g of azoisobutyronitrile in 1 1 of CCl4 is irradiated using a 300 W UV lamp for about 6 hours, whereby the reaction mixture is heated to boiling. 13 g of N-bromosuccinimide are then added and the mixture is irradiated for a further 8 hours. It is then cooled to room temperature and the precipitated succinimide is filtered off. The organic phase is then extracted with water, dried over MgSO4 and concentrated. The residue crystallizes and is stirred with cyclohexane. 300 g (68%) of the title compound are obtained as a beige solid.

Workup

  1. customis irradiated
  2. customfor about 6 hours
  3. temperaturewhereby the reaction mixture is heated to boiling
  4. customthe mixture is irradiated for a further 8 hours
  5. filtrationthe precipitated succinimide is filtered off
  6. extractionThe organic phase is then extracted with water
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customThe residue crystallizes

Sources & evidence

ORD record
ord-89711b3f381049feb1f6e41654cc64d2
Source dataset
uspto-grants-1999_02
Patent number
US05869517

Reaction notes

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