Dimethylcarbamoyl Chloride → N'-(4-bromo-2-fluorobenzyl)-N,N-dimethylurea

HRID 500186

Reaction equation

HRID 500186 reaction equation
[CH3:1][N:2]([CH3:6])[C:3](Cl)=[O:4].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][NH2:15])=[C:10]([F:16])[CH:9]=1.C(N(CC)CC)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][NH:15][C:3](=[O:4])[N:2]([CH3:6])[CH3:1])=[C:10]([F:16])[CH:9]=1

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 3770848(4-Bromo-2-fluorophenyl)methanamine

Product 1

HCID 67225137N'-(4-bromo-2-fluorobenzyl)-N,N-dimethylurea

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

N,N-Dimethylcarbamoyl chloride (101 μL, 1.1 mmol) was added to a solution of 1-(4-bromo-2-fluorophenyl)methanamine (0.204 g, 1.0 mmol) and triethylamine (148.1 μL, 1.10 mmol) in methylene chloride (5 mL) at 0° C., followed by 4-dimethylaminopyridine (0.012 g, 0.1 mmol). After 10 min, the ice-water bath was removed and the mixture was stirred overnight at RT. The mixture was washed with water and brine. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue (253 mg, 91.9%) was directly used in next step without further purification. LCMS: (M+H)=276.9/274.9.

Workup

  1. customthe ice-water bath was removed
  2. washThe mixture was washed with water and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue (253 mg, 91.9%) was directly used in next step without further purification

Sources & evidence

ORD record
ord-d0bc222f51e94dbab84bdf4c99763d31
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Linked notes

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