Dimethylcarbamoyl Chloride → N'-(4-Bromo-3-methylphenyl)-N,N-dimethylurea

HRID 1741061Notes

Reaction equation

HRID 1741061 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[CH3:9].C(N(CC)CC)C.[CH3:17][N:18]([CH3:22])[C:19](Cl)=[O:20]>CN(C)C1C=CN=CC=1.ClCCl>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:19](=[O:20])[N:18]([CH3:22])[CH3:17])=[CH:4][C:3]=1[CH3:9]

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 233594-Bromo-3-methylaniline

Product 1

HCID 13309167N'-(4-Bromo-3-methylphenyl)-N,N-dimethylureaYield 36.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

4-Bromo-3-methylaniline (5.00 g, 27 mmol), triethylamine (3.9 ml, 28 mmol), 4-(dimethylamino)pyridine (0.5 g, 4 mmol) and dimethylcarbamyl chloride (2.6 ml, 28 mmol) were mixed in dichloromethane (100 ml), and left to stand for 2 weeks. The solution was then washed with dilute hydrochloric acid, dried (Na2SO4) and evaporated to give a solid. This was triturated with ether, and the solid was filtered off and dried, affording the title compound (2.51 g, 36%) as an off-white solid.

Workup

  1. waitleft
  2. waitto stand for 2 weeks
  3. washThe solution was then washed with dilute hydrochloric acid
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customto give a solid
  7. customThis was triturated with ether
  8. filtrationthe solid was filtered off
  9. customdried

Sources & evidence

ORD record
ord-1955f43539e64b2591634fc1aac22dee
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

Loading…