Pyridine → N-(2-aminophenyl)-2-methoxy-5-trifluoromethanesulfonylbenzenesulfonamide

HRID 730202Notes

Reaction equation

HRID 730202 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])=[CH:5][C:4]=1[S:16](Cl)(=[O:18])=[O:17].[C:20]1([NH2:27])[C:21]([NH2:26])=[CH:22][CH:23]=[CH:24][CH:25]=1.N1C=CC=CC=1>ClCCl>[NH2:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[NH:27][S:16]([C:4]1[CH:5]=[C:6]([S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7243O-PhenylenediamineHCID 624992522-Methoxy-5-trifluoromethanesulfonyl-1-benzenesulfonyl chloride

Product 1

HCID 68948452N-(2-aminophenyl)-2-methoxy-5-trifluoromethanesulfonylbenzenesulfonamideYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-methoxy-5-trifluoromethanesulfonyl-1-benzenesulfonyl chloride (5 g) in dry dichloromethane (10 mL), benzene-1,2-diamine (5 g) was added followed by addition of dry pyridine (10 mL) at 0° C. The resulting deep red reaction mixture was then stirred at room temperature for 4 h. The reaction mixture was diluted with dichloromethane (250 mL). The contents were washed with saturated aqueous sodium chloride solution (50 mL) and saturated aqueous sodium carbonate solution (50 mL). The organic phase was dried over sodium sulfate and concentrated under vacuum. The residue obtained was purified by flash column chromatography eluting with DCM/EtOAc (7:1 to 4:1) to give N-(2-aminophenyl)-2-methoxy-5-trifluoromethanesulfonylbenzenesulfonamide (6 g). LC: Tr 0.95 min, MS: 411 (M+1)+. 1H NMR (CDCl3, 400 MHz): δ 4.18 (bs, 2H), 4.21 (s, 3H), 6.43 (m, 2H), 6.57 (bs, 1H), 6.75 (dd, 1H), 7.02 (t, 1H), 7.35 (d, 1H), 8.22 (dd, 1H), 8.40 (d, 1H) ppm.

Workup

  1. customThe resulting deep red reaction mixture
  2. washThe contents were washed with saturated aqueous sodium chloride solution (50 mL) and saturated aqueous sodium carbonate solution (50 mL)
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue obtained
  6. customwas purified by flash column chromatography
  7. washeluting with DCM/EtOAc (7:1 to 4:1)

Sources & evidence

ORD record
ord-5947a9a8f6b84f2aa59d49d6f26ef892
Source dataset
uspto-grants-2009_09
Patent number
US07582673B2

Reaction notes

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