Water → HCID 54343145, compound

HRID 620928Notes

Reaction equation

HRID 620928 reaction equation
Cl[CH2:2][C:3](=[O:18])[C:4]([NH:7][C:8](=[O:17])[C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([Cl:16])[CH:10]=1)([CH3:6])[CH3:5].[C-:19]#[N:20].[Na+].O.C(Cl)Cl>C(#N)C.C1OCCOCCOCCOCCOCCOC1>[C:19]([CH2:2][C:3](=[O:18])[C:4]([NH:7][C:8](=[O:17])[C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([Cl:16])[CH:10]=1)([CH3:6])[CH3:5])#[N:20]

Participants

7

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 8929Sodium CyanideHCID 54029353HCID 54029353, compound

Product 1

HCID 54343145HCID 54343145, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 6342AcetonitrileSolvent

Procedure

N-(3'-chloro-1',1'-dimethylacetonyl)-3,5-dichlorobenzamide (30 gm, 0.0972 m), sodium cyanide (15 gm, 0.306 m) and 18-crown-6 (1 gm) were dissolved in 300 ml of acetonitrile in a round bottom flask under a nitrogen atmosphere. The mixture was heated to reflux for about 4 hours. The contents of the flask were then cooled and transferred to a separatory funnel along with 100 ml of water and 500 ml of methylene chloride and mixed well. The aqueous layer was discarded and the organic layer was washed sequentially with water and brine, dried and the solvents stripped off to yield 12.5 gm of the product after recrystallization from methylene chloride and hexane.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for about 4 hours
  3. temperatureThe contents of the flask were then cooled
  4. additionmixed well
  5. washthe organic layer was washed sequentially with water and brine
  6. customdried

Sources & evidence

ORD record
ord-39846c1738f4450390c5a43c91f59f8e
Source dataset
uspto-grants-1989_04
Patent number
US04822902

Reaction notes

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