Methyl Isocyanate → 1-[1-(4-Bromo-phenyl)ethyl]-3-methyl-urea

HRID 858577Notes

Reaction equation

HRID 858577 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1.[CH3:11][N:12]=[C:13]=[O:14]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:10][C:13]([NH:12][CH3:11])=[O:14])[CH3:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 853000(R)-4-bromo-alpha-methylbenzylamine

Product 1

HCID 471273271-[1-(4-Bromo-phenyl)ethyl]-3-methyl-ureaYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred solution of (R)-(+)-1-(4-bromophenyl)ethylamine (0.5 g, 2.49 mmol) in anhydrous CH2Cl2 was added methyl isocyanate (0.15 mL, 2.49 mmol). The resulting solution was stirred at 25° C. overnight. CH2Cl2 was evaporate and residue partitioned between EtOAC and 1 N HCl. The organic layer was washed with H2O, brine and dried over Na2SO4. The solvent was removed in vacuo and the residue was purified by flash column chromatography (80% EtOAc in hexanes) to provide the desired product (0.60 g, 94%) as a white solid.

Workup

  1. customCH2Cl2 was evaporate
  2. customresidue partitioned between EtOAC and 1 N HCl
  3. washThe organic layer was washed with H2O, brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by flash column chromatography (80% EtOAc in hexanes)

Sources & evidence

ORD record
ord-2ab5911dda914485bf2df388fee5d0f1
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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