Ethyl Acetate → 2-(Benzylthio)-3-thiomorpholinopropan-1-amine

HRID 1960425Notes

Reaction equation

HRID 1960425 reaction equation
[CH2:1]([S:8][CH:9]([CH2:19][N:20]1[CH2:25][CH2:24][S:23][CH2:22][CH2:21]1)[CH2:10][NH:11]C(=O)OCCCC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C.C(OCC)(=O)C.Cl>CO>[CH2:1]([S:8][CH:9]([CH2:19][N:20]1[CH2:21][CH2:22][S:23][CH2:24][CH2:25]1)[CH2:10][NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21866389Hydrogen chloride-ethyl acetateHCID 86761802Butyl[2-(benzylthio)-3-thiomorpholinopropyl]carbamate

Product 1

HCID 574762142-(Benzylthio)-3-thiomorpholinopropan-1-amineYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tent-butyl [2-(benzylthio)-3-thiomorpholinopropyl]carbamate (21.46 g) in a mixed solvent of ethyl acetate (60 mL) and methanol (60 mL) was added hydrogen chloride-ethyl acetate solution (120 mL) at 0° C., and the mixture was stirred at room temperature for 4 hr. The reaction solution was concentrated, and the residue was partitioned between ethyl acetate and saturated aqueous potassium carbonate solution. The organic layer was washed with saturated brine, and dried over sodium sulfate, and the solvent was evaporated to give the title compound (14.41 g, yield 91%) as a yellow oil.

Workup

  1. concentrationThe reaction solution was concentrated
  2. customthe residue was partitioned between ethyl acetate and saturated aqueous potassium carbonate solution
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-dbbae337cdae48beb8e2c80966ba0e9e
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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