Ethyl Acetate → HCID 86607458, compound

HRID 2376608Notes

Reaction equation

HRID 2376608 reaction equation
[CH:1]1([N:7]([P:10]([O:15][CH2:16][CH3:17])([O:12][CH2:13][CH3:14])=[O:11])[CH:8]=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:27])=CC=1.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH:1]1([N:7]([P:10]([O:15][CH2:16][CH3:17])([O:12][CH2:13][CH3:14])=[O:11])[CH:8]=[S:27])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 87949Lawesson's reagentHCID 86607459HCID 86607459, compound

Product 1

HCID 86607458HCID 86607458, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 0.359 g (1.4 mmol) of N-(cyclohexyl)diethylphosphonoformamide, 0.276 g (0.7 mmol) of Lawesson Reagent in 10 ml toluene was refluxed for 5.5 hours. The resulting mixture was subjected to VLC (vacuum liquid chromatography) using gradient eluants (from 5% ethyl acetate in petroleum ether to ethyl acetate/petroleum ether (40:60) to give N-cyclohexyl diethylphosphonothioformamide as a yellow solid, 0.327 g (85.8%, isolated yield). NMR (CDCl3): 31P −1.66. 1H: 1.18-2.01 (m, 16H), 4.17 (m, 4H), 4.34 (m, 1H), 8.89 (br. s, 1H).

Workup

  1. temperaturewas refluxed for 5.5 hours
  2. customto give

Sources & evidence

ORD record
ord-cbb6161f3879424fafc91a134308db83
Source dataset
uspto-grants-2008_12
Patent number
US07468359B2

Reaction notes

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