Benzene → HCID 12822282, compound

HRID 614268Notes

Reaction equation

HRID 614268 reaction equation
C1C=CC=CC=1.[CH:7]([N:10]1[CH2:13][CH:12](CS([O-])(=O)=O)[CH2:11]1)([CH3:9])[CH3:8].[Na].[C:20]1([CH:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:27]#[N:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O.C1(C)C=CC=CC=1>[C:29]1([C:26]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([CH:12]2[CH2:13][N:10]([CH:7]([CH3:9])[CH3:8])[CH2:11]2)[C:27]#[N:28])[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

7

Reactant 4

HCID 241BenzeneHCID 6837DiphenylacetonitrileHCID 5360545SodiumHCID 20544158HCID 20544158, compound

Product 1

HCID 12822282HCID 12822282, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

The benzene solution of 1-isopropyl-3-azetidinylmethane sulfonate was added dropwise to the stirred refluxing toluene mixture containing the sodium salt of diphenylacetonitrile and refluxing continued for 1.5 hours after addition. The cooled reaction mixture was treated with water, the layers separated, and the organic layer extracted with dilute hydrochloric acid and water. The combined extracts were basified using dilute sodium hydroxide and the base insoluble material extracted with chloroform. The dried extract was concentrated and the residual material was recrystallized from isooctane. The α,α-diphenyl-α-(1-isopropyl-3-azetidinyl)acetonitrile weighed 142 g. (56%) and melted at 93°-95° C.

Workup

  1. temperaturerefluxing
  2. additionafter addition
  3. customThe cooled reaction mixture
  4. customthe layers separated
  5. extractionthe organic layer extracted with dilute hydrochloric acid and water
  6. extractionthe base insoluble material extracted with chloroform
  7. extractionThe dried extract
  8. concentrationwas concentrated
  9. customthe residual material was recrystallized from isooctane

Sources & evidence

ORD record
ord-3493347ae4b34532b53930a7fd875ab2
Source dataset
uspto-grants-1979_03
Patent number
US04144245

Reaction notes

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