Phosphorus sulfide (P2S5) → Tetradecanethioamide

HRID 1756984

Reaction equation

HRID 1756984 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 191.5%

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-8cd84f54b5e94abc80f94e0245c86aa6
Source dataset
uspto-grants-1995_08
Patent number
US05441975

Linked notes

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