Phosphorus sulfide (P2S5) → N-dodecylazepan-2-thione

HRID 1656893Notes

Reaction equation

HRID 1656893 reaction equation
[CH2:1]([N:13]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C:14]1=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:22]>C1C=CC=CC=1>[CH2:1]([N:13]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C:14]1=[S:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 42981Laurocapram

Product 1

HCID 10108679N-dodecylazepan-2-thioneYield 75.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 5 g (17.7 mmol) of 1-n-dodecylazacycloheptan-2-one in 150 ml of benzene was added 4.18 g (9.4 mmol) of phosphorus pentasulfide and the mixture was refluxed for 1 hr. After cooling to room temperature, the mixture was filtered and the solid was washed with chloroform and ethanol. The filtrate was concentrated in vacuo and the residue was subjected to flash chromatography, (silica; (95:5)V/V hexane/ethyl acetate) to give 2.11 g (40%) of 1-n-dodecylazacycloheptane-2thione.

Workup

  1. temperaturethe mixture was refluxed for 1 hr
  2. filtrationthe mixture was filtered
  3. washthe solid was washed with chloroform and ethanol
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-62f2298416ec4fd398b32b404b3188d3
Source dataset
uspto-grants-1993_10
Patent number
US05256647

Reaction notes

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