Hydrochloric Acid → 3-chloro-4-fluoro-N,N-dimethylbenzenesulfonamide

HRID 20545

Reaction equation

HRID 20545 reaction equation
[CH3:1][NH:2][CH3:3].C1COCC1.CCN(C(C)C)C(C)C.[Cl:18][C:19]1[CH:20]=[C:21]([S:26](Cl)(=[O:28])=[O:27])[CH:22]=[CH:23][C:24]=1[F:25].Cl>C(Cl)Cl.O>[Cl:18][C:19]1[CH:20]=[C:21]([S:26]([N:2]([CH3:3])[CH3:1])(=[O:27])=[O:28])[CH:22]=[CH:23][C:24]=1[F:25]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 1452223-Chloro-4-fluorobenzenesulphonyl chloride

Product 1

HCID 6977763-chloro-4-fluoro-N,N-dimethylbenzenesulfonamideYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 2M dimethylamine in THF (5.9 mL, 12 mmol) was diluted with DCM (25 mL) and cooled to 0° C. DIPEA (2.8 mL) was added, followed by and 3-chloro-4-fluorobenzenesulfonyl chloride (2.5 g, 11 mmol) in DCM (25 mL). The resulting mixture was allowed to warm to rt and stirred for 3 hours. Water (5 mL) and 1M hydrochloric acid (16 mL) was added. The organic phase was separated and evaporated under reduced pressure to afford the title compound (2.4 g, 94%).

Workup

  1. temperatureto warm to rt
  2. customThe organic phase was separated
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-089cb75a2f9c488fb48bf383b14768cf
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Linked notes

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