Thionyl Chloride → HCID 178527434, compound

HRID 1448045Notes

Reaction equation

HRID 1448045 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][CH:10]=[CH:11][N:12]=2)=[CH:4][CH:3]=1.[Cl:13][S:14](O)(=[O:16])=[O:15].S(Cl)(Cl)=O>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:12][CH:11]=[C:10]([S:14]([Cl:13])(=[O:16])=[O:15])[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 24638Chlorosulfonic acidHCID 2429482-(4-chlorophenyl)-1H-imidazole

Product 1

HCID 178527434HCID 178527434, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(4-chlorophenyl)imidazole (6 g., 0.034 mole) was added portionwise at room temperature with stirring to chlorosulfonic acid (30 ml.). The mixture was heated 2 hours at 100° and cooled to room temperature. Thionyl chloride (3 g.) was added and the mixture again heated for 2 hours at 100°. After cooling to room temperature the mixture was added cautiously to ice and water. A semi-solid separated and was extracted with ether. The ether layer was dried and concentrated to yield 2-(4-chlorophenyl)-4-chlorosulfonylimidazole (1.3 g., 0.005 mole).

Workup

  1. temperatureThe mixture was heated 2 hours at 100°
  2. temperaturethe mixture again heated for 2 hours at 100°
  3. temperatureAfter cooling to room temperature the mixture
  4. customA semi-solid separated
  5. extractionwas extracted with ether
  6. dry with materialThe ether layer was dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f2c209d9425941318c4f05341724244b
Source dataset
uspto-grants-1979_12
Patent number
US04179512

Reaction notes

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