Acetone Cyanohydrin → HCID 18978014, compound

HRID 2392997Notes

Reaction equation

HRID 2392997 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]([CH3:16])([CH3:15])[C:10](=[O:14])[CH2:11][C:12]#[N:13].[Cl:17][C:18]1[CH:26]=[C:25]([S:27][CH3:28])[CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21].CC(C)(O)C#N>ClCCl>[Cl:17][C:18]1[CH:26]=[C:25]([S:27][CH3:28])[CH:24]=[CH:23][C:19]=1[C:20](=[O:21])[CH:11]([C:12]#[N:13])[C:10](=[O:14])[C:9]([CH3:16])([CH3:15])[CH3:8]

Participants

6

Reactant 4

HCID 6406Acetone CyanohydrinHCID 8471TriethylamineHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 189779562-Chloro-4-methylsulphenylbenzoyl chloride

Product 1

HCID 18978014HCID 18978014, compoundYield 3.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (1.78 g) was added to a stirred solution of 4,4-dimethyl-3-oxopentanenitrile (2.0 g) in dichloromethane and the mixture was stirred at room temperature for 2 hours. A solution of 2-chloro-4-methylsulphenylbenzoyl chloride (3.02 g) in dichloromethane was added and the mixture stirred at room temperature overnight. Acetone cyanohydrin (1.36 g) was added and the mixture stirred for 4 days, then filtered. The filtrate was washed with hydrochloric acid (2M), water, aqueous sodium bicarbonate solution, water, then dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue purified by column chromatography (hexane, ethyl acetate and acetic acid). The main fraction was washed with aqueous sodium hydroxide (2M), water, dried and evaporated to dryness to give 1-(2-chloro-4-methylsulphenylphenyl)-2-cyano-4,4-dimethylpentan-1,3-dione (COMPOUND 664, 0.16 g) as a white solid, m.p. 97°-99° C.

Workup

  1. stirringthe mixture stirred at room temperature overnight
  2. stirringthe mixture stirred for 4 days
  3. filtrationfiltered
  4. washThe filtrate was washed with hydrochloric acid (2M), water, aqueous sodium bicarbonate solution, water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. customthe residue purified by column chromatography (hexane, ethyl acetate and acetic acid)
  9. washThe main fraction was washed with aqueous sodium hydroxide (2M), water
  10. customdried
  11. customevaporated to dryness

Sources & evidence

ORD record
ord-7faebabe8e2746b7b38e665e217a8562
Source dataset
uspto-grants-1998_09
Patent number
US05804532

Reaction notes

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