Hydrochloric Acid → HCID 69935099, compound

HRID 536054Notes

Reaction equation

HRID 536054 reaction equation
[F:1][C:2]1[CH:7]=[C:6](F)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[S:12]([NH:15][CH3:16])(=[O:14])=[O:13].Cl.[CH3:18][NH:19][CH3:20].C(N(CC)CC)C.Cl>C(Cl)Cl.O>[CH3:18][N:19]([CH3:20])[C:6]1[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]([S:12]([NH:15][CH3:16])(=[O:14])=[O:13])=[C:2]([F:1])[CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 29795223HCID 29795223, compound

Product 1

HCID 69935099HCID 69935099, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2,4-difluoro-N-methyl-5-nitrobenzenesulfonamide (8.0 g, 31.6 mmol) in CH2Cl2 (200 mL) at −20° C. was treated with dimethylamine hydrochloride (2.56 g, 31.6 mmol). The resulting mixture was treated dropwise with triethylamine and stirred for 1 hour before being treated with 15% aqueous HCl to adjust the pH to 3, diluted with water, and extracted with EtOAc. The organic extract was dried (sodium sulfate), concentrated, and subjected to flash chromatography (20-50% EtOAc-petroleum ether) to give 4-(dimethylamino)-2-fluoro-N-methyl-5-nitrobenzenesulfonamide (4.0 g, 46%) as a yellow solid. MS (m/z) 278.1 (M+H+).

Workup

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. dry with materialwas dried (sodium sulfate)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-834cae0cdbaa45398cd937405ca3287f
Source dataset
uspto-grants-2014_10
Patent number
US08859571B2

Reaction notes

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