Sodium Cyanide → HCID 18973689, compound

HRID 1780841Notes

Reaction equation

HRID 1780841 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=2[O:14][CH:15]([F:17])[F:16])[CH2:9]Cl)[CH2:3][CH2:2]1.[C-:18]#[N:19].[Na+]>CN(C)C=O>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH2:9][C:18]#[N:19])[CH:11]=[CH:12][C:13]=2[O:14][CH:15]([F:17])[F:16])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 18973686HCID 18973686, compound

Product 1

HCID 18973689HCID 18973689, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 3-cyclopropylmethoxy-4-difluoromethoxybenzyl chloride (26 g) in dimethylformamide (150 mL) under an argon atmosphere was added sodium cyanide (9.7 g, 198 mmol). The resulting mixture was stirred at room temperature and heated gently for 2 h, then cooled and concentrated. The mixture was partitioned between basic brine and ether and extracted twice. The organic extract was washed with brine and was dried (sodium sulfate). The solvent was removed in vacuo to provide an orange-brown oil (24 g), which was used without purification.

Workup

  1. temperatureheated gently for 2 h
  2. temperaturecooled
  3. concentrationconcentrated
  4. customThe mixture was partitioned between basic brine and ether
  5. extractionextracted twice
  6. extractionThe organic extract
  7. washwas washed with brine
  8. dry with materialwas dried (sodium sulfate)
  9. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-970195dbf7df4eb4b1d8e003b00b1379
Source dataset
uspto-grants-1997_05
Patent number
US05631286

Reaction notes

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