Methyl Isocyanate → HCID 58762667, compound

HRID 1453024Notes

Reaction equation

HRID 1453024 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]([C@H: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 58762667HCID 58762667, compoundYield 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 1N 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. 1H NMR (CDCl3) δ: 1.42 (d, J=7.0 Hz, 3H), 2.72 (d, J=4.9 Hz, 3H), 4.25 (brs, 1H), 4.73 (brs, 1H), 4.74-4.81 (m, 1H), 7.20 (d, J=8.3 Hz, 2H), 7.45 (d, J=8.3 Hz, 2H). ESIMS (MNa+): 258.

Workup

  1. customCH2Cl2 was evaporate
  2. customresidue partitioned between EtOAC and 1N 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-d2a9f0ae6f48415e920c4c6ae46cc4f6
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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