Sodium hydride → HCID 3775915, compound

HRID 1108999Notes

Reaction equation

HRID 1108999 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:13])=[CH:6][CH:5]=1.CC1C=CC(S([CH2:30][N+:31]#[C-:32])(=O)=O)=CC=1>C(OCC)C.CS(C)=O>[C:12]([C:11]1[C:10]([C:7]2[CH:6]=[CH:5][C:4]([Cl:3])=[CH:9][CH:8]=2)=[CH:30][NH:31][CH:32]=1)(=[O:13])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 953404-ChlorochalconeHCID 161915Tosylmethyl isocyanide

Product 1

HCID 3775915HCID 3775915, compoundYield 49.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A suspension of NaH (80% in paraffin) (3.97 g; 0.165 moles) in anhydrous ethyl ether (100 ml), maintained under nitrogen stream, is dropwise added with a solution of 3-(4-chlorophenyl)-1-phenyl-2-propen-1-one (18.11 g; 0075 moles) and tosylmethylisocianide (TOSMIC) (14.60 g; 0.075 moles) in anhydrous dimethylsulfoxide (170 ml) diluted with anhydrous ethyl ether (300 ml). Upon the additions are completed, the mixture is maintained under stirring at room temperature for 3 hours. After dilution with water (800 ml) the precipitate is filtered, washed with absolute ethanol and lastly with petroleum ether. There are obtained 10.40 g (yield 49.4%) of 4-benzoyl-3-(4-chlorophenyl)-1H-pyrrole, which is crystallized from N,N-dimethylformamide and water (m.p.: 232°-235° C.).

Workup

  1. temperaturemaintained under nitrogen stream
  2. temperaturethe mixture is maintained
  3. filtrationAfter dilution with water (800 ml) the precipitate is filtered
  4. washwashed with absolute ethanol and lastly with petroleum ether

Sources & evidence

ORD record
ord-4b876ff1596543c18aafae177df3a823
Source dataset
uspto-grants-1994_06
Patent number
US05318983

Reaction notes

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