Water → N-{2-[2-(cyanomethyl)-4,5-dimethoxyphenyl]ethyl}-2,2,2-trifluoroacetamide

HRID 76324Notes

Reaction equation

HRID 76324 reaction equation
[C-:1]#[N:2].[Na+].Cl[CH2:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH3:15])=[CH:8][C:7]=1[CH2:16][CH2:17][NH:18][C:19](=[O:24])[C:20]([F:23])([F:22])[F:21].O>CS(C)=O>[C:1]([CH2:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH3:15])=[CH:8][C:7]=1[CH2:16][CH2:17][NH:18][C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 86698208HCID 86698208, compound

Product 1

HCID 86698209N-{2-[2-(cyanomethyl)-4,5-dimethoxyphenyl]ethyl}-2,2,2-trifluoroacetamideYield 51%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

In a three-necked flask stir, at ambient temperature, a suspension of sodium cyanide (9.8 g, 200 mmoles) in 160 mL of DMSO. Add to the suspension, dropwise, a solution of N-{2-[2-(chloromethyl)-4,5-dimethoxyphenyl]ethyl}-2,2,2-trifluoroacetamide (26 g, 798 mmoles) in 80 mL of DMSO. After being in contact for 1 hour 30 minutes at ambient temperature, hydrolyse the mixture using 300 mL of water and extract the mixture with dichloromethane (3×150 mL). Combine the organic phases and wash them with 10% aqueous solution of NaOAc (150 mL) and saturated aqueous NaCl solution (4×150 mL), then dry them over MgSO4 and carry out drying in vacuo. The product obtained is recrystallised from toluene (66 mL) to obtain 12.8 g of a white powder corresponding to the title compound.

Workup

  1. additionAdd to the suspension
  2. extractionextract the mixture with dichloromethane (3×150 mL)
  3. washCombine the organic phases and wash them with 10% aqueous solution of NaOAc (150 mL) and saturated aqueous NaCl solution (4×150 mL)
  4. dry with materialdry them over MgSO4
  5. customcarry out drying in vacuo
  6. customThe product obtained
  7. customis recrystallised from toluene (66 mL)

Sources & evidence

ORD record
ord-f9eddb143a0f4efb9f6d656a9c8e7270
Source dataset
uspto-grants-2014_09
Patent number
US08835627B2

Reaction notes

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