Dabco → 3-chloro-4-fluoro-N-pyrimidin-4-ylbenzenesulfonamide

HRID 46340

Reaction equation

HRID 46340 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][N:3]=1.C1N2CCN(CC2)C1.[Cl:16][C:17]1[CH:18]=[C:19]([S:24](Cl)(=[O:26])=[O:25])[CH:20]=[CH:21][C:22]=1[F:23]>C(#N)C>[Cl:16][C:17]1[CH:18]=[C:19]([S:24]([NH:1][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][N:3]=2)(=[O:25])=[O:26])[CH:20]=[CH:21][C:22]=1[F:23]

Participants

5

Reactant 3

HCID 9237DabcoHCID 689584-AminopyrimidineHCID 1452223-Chloro-4-fluorobenzenesulphonyl chloride

Product 1

HCID 594364913-chloro-4-fluoro-N-pyrimidin-4-ylbenzenesulfonamideYield 27%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Aminopyrimidine (1.0 g, 10.5 mmol) and DABCO™ (1.18 g, 10.5 mmol) were added concurrently to a solution of 3-chloro-4-fluorobenzenesulfonyl chloride (1.25 mL, 10.0 mmol) in anhydrous acetonitrile (49 mL). The reaction mixture immediately turned yellow and a precipitate was formed. After stirring for 16 hours, the mixture was concentrated in vacuo. The crude material was suspended in ethyl acetate (75 mL) and water (75 mL) and stirred for 15 minutes. The resulting solid was filtered and dried in vacuo to afford the title compound, 0.83 g, 27% yield.

Workup

  1. customThe reaction mixture immediately turned yellow and a precipitate was formed
  2. concentrationthe mixture was concentrated in vacuo
  3. stirringwater (75 mL) and stirred for 15 minutes
  4. filtrationThe resulting solid was filtered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-257ca3bd31f446f79a741ae7a987f53f
Source dataset
uspto-grants-2013_09
Patent number
US08541588B2

Linked notes

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