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

HRID 1946687

Reaktionsgleichung

Reaktionsgleichung von HRID 1946687
[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-63d91eb43cb744e2bacee07bdfb9baf8
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399448B2

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