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

HRID 1587478Notes

Reaction equation

HRID 1587478 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 40%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 5g (17.7mmol) of 1-n-dodecylazacycloheptan-2-one in 150ml of benzene was added 4.18g (9.4mmol) 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.llg (40%) of 1-n-dodecylazacycloheptane-2-thione.

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-502ff0342b0a44e6b0a104d39a13916c
Source dataset
uspto-grants-1993_06
Patent number
US05218113

Reaction notes

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