Dimethylamine → HCID 20299643, compound

HRID 1733471Notes

Reaction equation

HRID 1733471 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1.S(Cl)(Cl)=O.[CH3:15][NH:16][CH3:17].Cl[S:19](O)(=[O:21])=[O:20]>>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:6]([C:8]([S:19](=[O:21])(=[O:20])[N:16]([CH3:17])[CH3:15])=[CH:9][N:10]=2)[CH:7]=1

Participants

5

Reactant 4

HCID 674DimethylamineHCID 24386Thionyl ChlorideHCID 24638Chlorosulfonic acidHCID 128415726-Chloroimidazo[1,2-a]pyrazine

Product 1

HCID 20299643HCID 20299643, compound

Conditions

Temperature
100 °C

Procedure

6-Chloroimidazo[1,2-a]pyrazine (3.07 g, 0.020 mole) is added in portions with stirring to 20 ml chlorosulfonic acid, and the mixture heated 2 hours at 100° C. and then cooled to room temperature. Thionyl chloride (2 g) is added and the mixture reheated to 100° C. for 2 hours. After cooling to room temperature, the mixture is quenched on crushed ice and extracted with ether. The ether layer is dried over sodium sulfate, filtered and concentrated under vacuum to give an oil which is stirred with a mixture of crushed ice and aqueous dimethylamine for one hour. The crude 6-chloro-3-(N,N-dimethylsulfamoyl)imidazo[1,2-a]pyrazine is collected by filtration.

Workup

  1. temperaturecooled to room temperature
  2. temperatureAfter cooling to room temperature
  3. customthe mixture is quenched
  4. customon crushed ice
  5. extractionextracted with ether
  6. dry with materialThe ether layer is dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customto give an oil which
  10. filtrationThe crude 6-chloro-3-(N,N-dimethylsulfamoyl)imidazo[1,2-a]pyrazine is collected by filtration

Sources & evidence

ORD record
ord-7c3a96f302614c9393b0c6b60f716485
Source dataset
uspto-grants-1980_12
Patent number
US04242344

Reaction notes

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