3-Amino-1-propanol → HCID 14745382, compound

HRID 977042Notes

Reaction equation

HRID 977042 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].[Cl:6][C:7]([Cl:14])([Cl:13])[C:8]([N:10]=[C:11]=[O:12])=[O:9]>O.CC(C)=O>[Cl:6][C:7]([Cl:14])([Cl:13])[C:8]([NH:10][C:11]([NH:1][CH2:2][CH2:3][CH2:4][OH:5])=[O:12])=[O:9]

Participants

5

Reactant 2

HCID 90863-Amino-1-propanolHCID 76400Trichloroacetyl isocyanate

Product 1

HCID 14745382HCID 14745382, compoundYield 58.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

3.75 g of 3-aminopropanol are dissolved in a mixture of 10 g of water and 10 g of acetone. 9.4 g of trichloroacetyl isocyanate are subsequently added dropwise. After a slightly exothermic reaction, the mixture is stirred for 1 hour at room temperature, then refluxed for 2.5 hours. Concentration in a rotary evaporator gives 7.7 g of an oily phase, which is taken up in acetone and subjected to column chromatography on silica gel using cyclohexane/ethyl acetate (1:1) as eluent.

Workup

  1. customAfter a slightly exothermic reaction
  2. temperaturerefluxed for 2.5 hours
  3. concentrationConcentration
  4. customin a rotary evaporator

Sources & evidence

ORD record
ord-6799a6ce5fc84802bad07594e3ff051f
Source dataset
uspto-grants-1997_03
Patent number
US05614351

Reaction notes

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