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

HRID 1946687

Reaction equation

HRID 1946687 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-63d91eb43cb744e2bacee07bdfb9baf8
Source dataset
uspto-grants-2013_03
Patent number
US08399448B2

Linked notes

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