Acetone Cyanohydrin → HCID 11309731, compound

HRID 423025Notes

Reaction equation

HRID 423025 reaction equation
C[Si]([N-:5][Si](C)(C)C)(C)C.[Li+].[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1.OC(C)(C)[C:22]#[N:23]>C1COCC1>[NH2:5][CH:16]([C:15]1[CH:18]=[CH:19][C:12]([Cl:11])=[CH:13][CH:14]=1)[C:22]#[N:23]

Participants

5

Reactant 3

HCID 6406Acetone CyanohydrinHCID 77264-ChlorobenzaldehydeHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 11309731HCID 11309731, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium bis(trimethylsilyl)amide (42.7 mL) was added to 4-chlorobenzaldehyde (5 g) in THF (100 mL) at −40° C. under nitrogen. The resulting solution was warmed to room temperature and stirred for 4 hours. α-Hydroxyisobutyronitrile (acetone cyanohydrin, 6.50 mL) was then added, and the reaction mixture was stirred at 25° C. for a further 12 hours, then quenched with saturated NaHCO3 (50 mL), extracted with EtOAc (3×100 mL), the organic layer was dried over MgSO4, filtered and evaporated. The crude material was then purified by flash silica chromatography, elution gradient 0 to 100% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford 2-amino-2-(4-chlorophenyl)acetonitrile as a colourless oil, which solidified on standing to give a white solid (3.40 g, 57.4%).

Workup

  1. stirringthe reaction mixture was stirred at 25° C. for a further 12 hours
  2. customquenched with saturated NaHCO3 (50 mL)
  3. extractionextracted with EtOAc (3×100 mL)
  4. dry with materialthe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude material was then purified by flash silica chromatography, elution gradient 0 to 100% EtOAc in isohexane
  8. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-610751ce980e4193b400ea30d9ea8921
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

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