Phosphorus sulfide (P2S5) → Tetradecanethioamide

HRID 264128

Reaction equation

HRID 264128 reaction equation
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:2].[C:15]([NH2:30])(=O)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>C1COCC1>[C:15](=[S:2])([NH2:30])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 69492Tetradecanamide

Product 1

HCID 21469509TetradecanethioamideYield 105.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phosphorus pentasulfide (9.8 g, 0.044 mol) was added to a mixture of tetradecanamide (8.6 g, 0.04 mol) in dry THF (250 mL) and the mixture refluxed overnight, concentrated in vacuo, and heated with methanol (200 mL), filtered, and the filtrate concentrated in vacuo to yield a pale yellow solid (10.28 g, 99%) used without further purification.

Workup

  1. temperaturethe mixture refluxed overnight
  2. concentrationconcentrated in vacuo
  3. temperatureheated with methanol (200 mL)
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-4ff015936dad43c28e0d560ebd8cf89e
Source dataset
uspto-grants-1997_07
Patent number
US05646170

Linked notes

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