Water → HCID 22176574, compound

HRID 1797195Notes

Reaction equation

HRID 1797195 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[Br:6][C:7]1[CH:15]=[CH:14][C:10]([CH2:11][CH2:12][NH2:13])=[CH:9][CH:8]=1.C([O-])([O-])=O.[Na+].[Na+].O>CC(C)=O>[Br:6][C:7]1[CH:15]=[CH:14][C:10]([CH2:11][CH2:12][NH:13][C:2]([O:4][CH3:5])=[O:3])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 10340Sodium CarbonateHCID 533915p-Bromophenethylamine

Product 1

HCID 22176574HCID 22176574, compoundYield 110.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Into a 50 mL-single neck flask, 260 mg of methyl chloroformate in acetone (5 mL) was added dropwise to 500 mg of 4-bromophenethyl amine and 291 mg of Na2CO3 in acetone (20 mL) while stirring at room temperature under a nitrogen atmosphere. The reaction was then stirred overnight at this temperature. In the morning, the mixture was poured into H2O and the desired product was extracted with ethyl acetate. This organic layer was washed with H2O, dried over Na2SO4, and concentrated under reduced vacuum to yield the intermediate title compound (714 mg) as a white solid. This material was taken to the next reaction without further purification. Ion spray M.S. 259.2 (M*+1).

Workup

  1. stirringThe reaction was then stirred overnight at this temperature
  2. extractionthe desired product was extracted with ethyl acetate
  3. washThis organic layer was washed with H2O
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced vacuum

Sources & evidence

ORD record
ord-8d628f9dc8664b849d9d8a77a86aadec
Source dataset
uspto-grants-2006_04
Patent number
US07034045B1

Reaction notes

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