4-Methylmorpholine → n-{3-Nitro-4-(3,5-bis-trifluoromethyl-benzylamino)-phenyl}-benzenesulphonamide

HRID 840095Notes

Reaction equation

HRID 840095 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19].[F:21][C:22]([F:36])([F:35])[C:23]1[CH:24]=[C:25]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[CH2:26][NH2:27].CN1CCOCC1>CS(C)=O.C(OCC)(=O)C>[N+:18]([C:3]1[CH:4]=[C:5]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:6]=[CH:7][C:2]=1[NH:27][CH2:26][C:25]1[CH:28]=[C:29]([C:31]([F:32])([F:33])[F:34])[CH:30]=[C:23]([C:22]([F:21])([F:35])[F:36])[CH:24]=1)([O-:20])=[O:19]

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 5210993,5-Bis(trifluoromethyl)benzylamineHCID 4599069N-(4-fluoro-3-nitrophenyl)benzenesulfonamide

Product 1

HCID 22621842n-{3-Nitro-4-(3,5-bis-trifluoromethyl-benzylamino)-phenyl}-benzenesulphonamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-{4-fluoro-3-nitro-phenyl}-benzenesulphonamide (3.0 g, 10 mmol), 3,5-bis-trifluoromethylbenzylamine (3.0 g, 12.5 mmol) and N-methylmorpholine (2.2 mL, 20 mmol) in 25 mL dimethylsulphoxide are kept for 6 h at 60-100° C., diluted with 150 mL ethyl acetate, washed with water, dilute hydrochloric acid and water again, dried and concentrated by evaporation until not quite dry. The residue is combined with 80 mL EtOH and evaporated down to a residual volume of about 50 mL. The crystals precipitated after cooling are filtered off and washed with EtOH and petroleum ether.

Workup

  1. washwashed with water, dilute hydrochloric acid and water again
  2. customdried
  3. concentrationconcentrated by evaporation until not
  4. customquite dry
  5. customevaporated down to a residual volume of about 50 mL
  6. customThe crystals precipitated
  7. temperatureafter cooling
  8. filtrationare filtered off
  9. washwashed with EtOH and petroleum ether

Sources & evidence

ORD record
ord-85ceb8881f0148d7b79e1914119d07d7
Source dataset
uspto-grants-2002_04
Patent number
US06365584B1

Reaction notes

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