Dimethyl Sulfoxide → HCID 13067089, compound

HRID 647614Notes

Reaction equation

HRID 647614 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[C:4]([C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[CH:13]=[CH:14][C:15]#[N:16])=[O:5].S([CH:31]([N+:33]#[C-])C)(C1C=CC(C)=CC=1)(=O)=O.CS(C)=O.[H-].[Na+].[CH3:41][CH2:42]OCC>O>[F:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[C:4]([C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[C:13]1[C:14]([C:31]#[N:33])=[CH:15][NH:16][C:41]=1[CH3:42])=[O:5]

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 3283Diethyl Ether2×HCID 24758Sodium hydrideHCID 110528851-(1-Isocyanoethanesulfonyl)-4-methylbenzeneHCID 539727423-[4-Chloro-2-(2-fluorobenzoyl)phenyl]prop-2-enenitrile

Product 1

HCID 13067089HCID 13067089, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 34.5 g (121 mmole) of 3-[2-(2-fluorobenzoyl)-4-chlorophenyl]-2-propenenitrile, 25.3 g (121 mmole) of 1-tosylethyl isocyanide, 200 ml of dimethyl sulfoxide and 400 ml of ether was added dropwise to a suspension of 8.9 g (184 mmole) of 50% sodium hydride in mineral oil and 450 ml of ether. When the addition was complete stirring was continued for 2 hr. The mixture was diluted with water and the ether layer was separated. The aqueous solution was extracted with ether. The combined ether extracts were washed with water, dried over anhydrous sodium sulfate, and concentrated at reduced pressure to give a dark oil. Crystallization from ether gave off-white crystals. A small portion was recrystallized from a mixture of methylene chloride and ether to give colorless prisms, mp 201°-202°.

Workup

  1. additionWhen the addition
  2. customthe ether layer was separated
  3. extractionThe aqueous solution was extracted with ether
  4. washThe combined ether extracts were washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated at reduced pressure
  7. customto give a dark oil
  8. customCrystallization from ether
  9. customgave off-white crystals
  10. customA small portion was recrystallized from a mixture of methylene chloride and ether
  11. customto give colorless prisms, mp 201°-202°

Sources & evidence

ORD record
ord-9c3f739d708041788ba60f14694c29db
Source dataset
uspto-grants-1983_10
Patent number
US04409390

Reaction notes

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