4-Methoxybenzaldehyde → 3-(4-Methoxyphenyl)-2-(morpholin-4-ylcarbonothioyl)acrylonitrile

HRID 572604Notes

Reaction equation

HRID 572604 reaction equation
[N:1]1([C:7](=[S:11])[CH2:8][C:9]#[N:10])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH:12](=O)[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1>N1CCCCC1.C(O)C>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([CH:12]=[C:8]([C:7]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[S:11])[C:9]#[N:10])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 312444-MethoxybenzaldehydeHCID 451589413-Morpholin-4-yl-3-thioxopropanenitrile

Product 1

HCID 866375463-(4-Methoxyphenyl)-2-(morpholin-4-ylcarbonothioyl)acrylonitrile

Reagents, catalysts & solvents 1

HCID 21975547Piperidine ethanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 3-morpholin-4-yl-3-thioxopropanenitrile (0.122 g, 0.72 mmol) and p-anisaldehyde (0.1 mL, 0.86 mmol) in 10% piperidine/ethanol (5.5 mL) was allowed to stir at 50° C. under nitrogen for 3.5 h. The reaction mixture was concentrated and the residue was diluted with 10% citric acid solution and extracted with EtOAc. The organic solutions were combined, washed with sat NaHCO3 and brine, dried over MgSO4, filtered and concentrated to give 3-(4-methoxyphenyl)-2-(morpholin-4-ylcarbonothioyl)acrylonitrile. The crude product was a mixture of stereoisomers and was used directly in the next step. LCMS: (AA) ES+ 289.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue was diluted with 10% citric acid solution
  3. extractionextracted with EtOAc
  4. washwashed with sat NaHCO3 and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0112e1f079454427860a6b13037ae33c
Source dataset
uspto-grants-2015_05
Patent number
US09029411B2

Reaction notes

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