Chlorosulfonic acid → 4-(6-Chloropyrimidine-4-carboxamido)-3-methylbenzene-1-sulfonyl chloride

HRID 1746669

Reaktionsgleichung

Reaktionsgleichung von HRID 1746669
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])=[O:9])[CH:3]=1.[Cl:18][S:19](O)(=[O:21])=[O:20]>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([S:19]([Cl:18])(=[O:21])=[O:20])=[CH:13][C:12]=2[CH3:17])=[O:9])[CH:3]=1

Komponenten

4

Edukt 2

HCID 24638Chlorosulfonic acidHCID 594470936-chloro-N-(2-methylphenyl)pyrimidine-4-carboxamide2×

Produkt 1

HCID 594468454-(6-Chloropyrimidine-4-carboxamido)-3-methylbenzene-1-sulfonyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A cooled (0° C.) solution of 6-chloro-N-(2-methylphenyl)pyrimidine-4-carboxamide (Intermediate 18; 14.00 g; 56.52 mmol) in DCM (280 ml) was treated dropwise with a solution of chlorosulfonic acid (37.8 ml; 565 mmol) in DCM (100 mL). The reaction mixture was allowed to warm from 0° C. to room temperature, then it was stirred at room temperature overnight. The mixture was cooled to 15° C., a mixture ice/water was added and it was stirred for a few minutes. Phases were separated and the organic layer was washed with cold water, brine, dried over MgSO4, filtered and concentrated under vacuum to afford the title compound as a beige solid.

Aufarbeitung

  1. temperatureto warm from 0° C. to room temperature
  2. temperatureThe mixture was cooled to 15° C.
  3. stirringit was stirred for a few minutes
  4. customPhases were separated
  5. washthe organic layer was washed with cold water, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-33861456a9e24069b46105b31d7aed97
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150519B2

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