Dimethyl Sulfoxide → 4-(2-Benzoyl-4-chlorophenyl)-1H-pyrrole-3-carbonitrile

HRID 2296301Notes

Reaction equation

HRID 2296301 reaction equation
[C:1]([C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[CH:16]=[CH:17][C:18]#[N:19])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S([CH2:30][N+:31]#[C-])(C1C=CC(C)=CC=1)(=O)=O.[CH3:33]S(C)=O.[H-].[Na+]>O.CCOCC>[C:1]([C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[C:16]1[C:17]([C:30]#[N:31])=[CH:18][NH:19][CH:33]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 161915Tosylmethyl isocyanideHCID 543140203-(2-Benzoyl-4-chlorophenyl)prop-2-enenitrile

Product 1

HCID 130670864-(2-Benzoyl-4-chlorophenyl)-1H-pyrrole-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A mixture of 10.7 g (40 mmole) of 3-(2-benzoyl-4-chlorophenyl)-2-propenenitrile, 5.3 g (38 mmole) of tosylmethyl isocyanide, 75 ml of dimethyl sulfoxide and 150 ml of ether was added dropwise to a suspension of 3.7 g (77 mole) of 50% sodium hydride in mineral oil and 170 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 green oil. Purification by column chromatography (800 g silica gel; eluent 5% ether in methylene chloride) gave end product as off-white prisims, mp 175°-177°.

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. concentrationand concentrated at reduced pressure
  7. customto give a dark green oil
  8. customPurification by column chromatography (800 g silica gel; eluent 5% ether in methylene chloride)
  9. customgave end product as off-white prisims, mp 175°-177°

Sources & evidence

ORD record
ord-8d871d9412b248d9a9a555c484bd6053
Source dataset
uspto-grants-1984_01
Patent number
US04428879

Reaction notes

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