Sodium Cyanide → HCID 67343329, compound

HRID 1671607Notes

Reaction equation

HRID 1671607 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:14]Br)[C:5](=[O:13])[N:6]([CH2:8][C:9]([F:12])([F:11])[F:10])[CH:7]=1.[C-:16]#[N:17].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH2:14][C:16]#[N:17])[C:5](=[O:13])[N:6]([CH2:8][C:9]([F:12])([F:11])[F:10])[CH:7]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 67342880HCID 67342880, compound

Product 1

HCID 67343329HCID 67343329, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Bromo-3-(bromomethyl)-1-(2,2,2-trifluoroethyl)pyridin-2(1H)-one (1.40 g, 4.01 mmol) was added in portions over 15 min to a solution of sodium cyanide (1.48 g, 30.1 mmol) in methanol (15 mL). After 1 h, the reaction was concentrated to dryness, diluted with water, extracted with dichloromethane (3×), and the combined organic extracts were dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane >5% methanol/dichloromethane) gave the title compound (0.740 g). MS 296.9 (M+1).

Workup

  1. concentrationthe reaction was concentrated to dryness
  2. additiondiluted with water
  3. extractionextracted with dichloromethane (3×)
  4. dry with materialthe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography (100% dichloromethane >5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-122b02f6f65643cc8db37f695db7897a
Source dataset
uspto-grants-2011_08
Patent number
US07994325B2

Reaction notes

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