Hydrochloric Acid → HCID 19825145, compound

HRID 727821Notes

Reaction equation

HRID 727821 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[CH:11][N:12]([S:14](=[O:19])(=[O:18])[N:15]([CH3:17])[CH3:16])[CH:13]=1.C([Li])CCC.CN(C)[CH:27]=[O:28].Cl>O1CCCC1.CCCCCC>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([CH:27]=[O:28])[N:12]([S:14](=[O:18])(=[O:19])[N:15]([CH3:16])[CH3:17])[CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 14691486HCID 14691486, compoundHCID 178418339Butyllithium

Product 1

HCID 19825145HCID 19825145, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To 4-(2,4-Dichlorophenyl)-1-(dimethylsulphamoyl)imidazole, (8.0 g) in tetrahydrofuran (125ml), maintained under a dry nitrogen atmosphere at -60° was added 2.6M butyllithium in hexane (10.57 ml). The solution was stirred and after a short time dimethylformamide (2.9 ml) was added. The mixture was warmed slowly to room temperature and then added to dilute hydrochloric acid. The product was extracted with ethyl acetate and the extract washed with water, dried the solvent evaporated and the solid residue recrystallised from toluene to give 4-(2,4-dichlorophenyl)-1-(dimethylsulphamoyl)-2-formylimidazole, m.p. 148°-157° (dec.).

Workup

  1. extractionThe product was extracted with ethyl acetate
  2. washthe extract washed with water
  3. customdried the solvent
  4. customevaporated
  5. customthe solid residue recrystallised from toluene

Sources & evidence

ORD record
ord-14fde966441442b1ad537dc69866d380
Source dataset
uspto-grants-1991_09
Patent number
US05045557

Reaction notes

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