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

HRID 981455

Reaction equation

HRID 981455 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 2.11g (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-d61690ac4ec3412db40a9f929e80f768
Source dataset
uspto-grants-1991_02
Patent number
US04992422

Linked notes

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