Triethylamine → HCID 14691486, compound

HRID 727827Notes

Reaction equation

HRID 727827 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][NH:12][CH:13]=1.C(N(CC)CC)C.[CH3:21][N:22]([CH3:27])[S:23](Cl)(=[O:25])=[O:24]>O1CCCC1.C(OCC)(=O)C>[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:23](=[O:25])(=[O:24])[N:22]([CH3:27])[CH3:21])[CH:13]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 178477961HCID 178477961, compound

Product 1

HCID 14691486HCID 14691486, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(2,4-dichlorophenyl)-1H-imidazole (12.14 g), triethylamine (13 ml) and dimethylsulphamoyl chloride (7.5 ml) in tetrahydrofuran (50 ml) was stirred for 18 hours at room temperature and then heated under reflux until almost no starting material remained. The organic phase was diluted with ethyl acetate (300 ml), washed with dilute hydrochloric acid, water and aqueous sodium bicarbonate, dried and the solvent evaporated to give an oily solid which was treated to flash column chromatography and the product recrystallised to give 4-(2,4-dichlorophenyl)-1-(dimethylsulphamoyl)imidazole, m.p. 169°-171°.

Workup

  1. temperatureheated
  2. temperatureunder reflux until almost no starting material
  3. washwashed with dilute hydrochloric acid, water and aqueous sodium bicarbonate
  4. customdried
  5. customthe solvent evaporated
  6. customto give an oily solid which
  7. additionwas treated to flash column chromatography
  8. customthe product recrystallised

Sources & evidence

ORD record
ord-b22ea3bacac446bab2d5baff1cc40d9b
Source dataset
uspto-grants-1991_09
Patent number
US05045557

Reaction notes

Loading…