Water → HCID 23507525, compound

HRID 1373121Notes

Reaction equation

HRID 1373121 reaction equation
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7].[H-].[Na+].F[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1.O>CN(C=O)C>[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][N:5]([C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1)[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:7])=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 2478570N-[2-(dimethylamino)ethyl]benzenesulfonamide

Product 1

HCID 23507525HCID 23507525, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6.8 g (29.8 mmol) of N-(2-dimethylamino-ethyl)-phenylsulphonamide are dissolved in 100 ml of DMF and combined with 1.3 g (30 mmol) of sodium hydride (55% in oil). The mixture is stirred for one hour at ambient temperature. Then 4.2 g (29.8 mmol) of 4-fluoro-nitrobenzene are added, and stirring is continued for another 16 hours. After the addition of 300 ml of water the mixture is extracted with ethyl acetate. The organic phase is washed with water, dried and evaporated down. The residue is acidified with 1 N hydrochloric acid and washed with ethyl acetate. The aqueous phase is then made basic again with sodium hydroxide solution and extracted with ethyl acetate. The organic phase is dried and evaporated down.

Workup

  1. stirringstirring
  2. waitis continued for another 16 hours
  3. extractionis extracted with ethyl acetate
  4. washThe organic phase is washed with water
  5. customdried
  6. customevaporated down
  7. washwashed with ethyl acetate
  8. extractionextracted with ethyl acetate
  9. customThe organic phase is dried
  10. customevaporated down

Sources & evidence

ORD record
ord-2c445b79523945e9829d8614a259dc6c
Source dataset
uspto-grants-2007_01
Patent number
US07160901B2

Reaction notes

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