Water → HCID 19823712, compound

HRID 728253Notes

Reaction equation

HRID 728253 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]=O)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl.[CH3:15][NH:16][CH3:17].[C-:18]#[N:19].[Na+].O>CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]([N:16]([CH3:17])[CH3:15])[C:18]#[N:19])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8929Sodium CyanideHCID 10473Dimethylamine, hydrochlorideHCID 99423881-(4-Chlorophenyl)cyclobutanecarbaldehyde

Product 1

HCID 19823712HCID 19823712, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A mixture of 1-(4-chlorophenyl)cyclobutanecarbaldehyde (13.7 g), dry dimethylamine hydrochloride (6.6 g) and dry dimethylsulphoxide (50 ml) was added dropwise to a stirred mixture of sodium cyanide (3.9 g) in dry dimethylsulphoxide (100 ml). The mixture was stirred for 66 hours at ambient temperature and the reaction mixture was poured into water. The mixture was extracted with ether and the ether solution was then extracted with dilute hydrochloric acid. The aqueous phase was basified and extracted with ether. Removal of the ether gave 2-[1-(4-chlorophenyl)cyclobutyl]-2-dimethylaminoacetonitrile (m.p. 90°-91° C.).

Workup

  1. extractionThe mixture was extracted with ether
  2. extractionthe ether solution was then extracted with dilute hydrochloric acid
  3. extractionextracted with ether
  4. customRemoval of the ether

Sources & evidence

ORD record
ord-d0570266543148c4b6264b1d72aee61b
Source dataset
uspto-grants-1991_09
Patent number
US05047432

Reaction notes

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