Water → Methyl phenethylcarbamate

HRID 1450271

Reaction equation

HRID 1450271 reaction equation
[CH2:1]([NH2:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.Cl[CH2:18][O:19][CH:20]=[O:21].O>O1CCCC1>[CH3:18][O:19][C:20]([NH:9][CH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 1001PhenethylamineHCID 8471TriethylamineHCID 17803410Chloromethyl formate

Product 1

HCID 4380476Methyl phenethylcarbamateYield 97.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold solution consisting of phenethylamine (20g,0.16mol) in tetrahydrofuran (900 mL) was added triethylamine (23 mL, 0.16 mol). To this solution was added dropwise chloromethylformate (64 mL, 0.8 mol). The reaction mixture was then stirred overnight water (450 mL) was added and the layers were separated. The organic layer was washed successively with water (1×200mL) and brine (1×200mL). The organic solvent was dried (anhydrous magnesium sulfate), filtered and concentrated to give the title compound (28 g, 94% yield).

Workup

  1. additionwas added
  2. customthe layers were separated
  3. washThe organic layer was washed successively with water (1×200mL) and brine (1×200mL)
  4. dry with materialThe organic solvent was dried (anhydrous magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7ba537965e054dbcaf88d63a2f6e216f
Source dataset
uspto-grants-1997_02
Patent number
US05602145

Linked notes

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