HCID 68949241, compound → HCID 68951993, compound

HRID 730210Notes

Reaction equation

HRID 730210 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]([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[NH:26][S:27]([C:30]1[CH:35]=[CH:34][C:33]([N+:36]([O-])=O)=[CH:32][CH:31]=1)(=[O:29])=[O:28])(=[O:18])=[O:17]>CC(O)=O.CCOC(C)=O.[Fe]>[NH2:36][C:33]1[CH:32]=[CH:31][C:30]([S:27]([NH:26][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[NH:19][S:16]([C:4]2[CH:5]=[C:6]([S:9]([C:12]([F:15])([F:14])[F:13])(=[O:10])=[O:11])[CH:7]=[CH:8][C:3]=2[O:2][CH3:1])(=[O:17])=[O:18])(=[O:29])=[O:28])=[CH:35][CH:34]=1

Participants

5

Reactant 1

HCID 68949241HCID 68949241, compound

Product 1

HCID 68951993HCID 68951993, compoundYield 85.9%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of the 2-methoxy-N-[2-(4-nitrobenzenesulfonylamino)phenyl]-5-trifluoromethanesulfonylbenzenesulfonamide (1 mmol) in AcOH (5 mL), iron powder (300 mg) was added and the resulting reaction mixture was heated at 100° C. for 30 min. The reaction mixture was filtered through a short pad of Celite and the pad was washed with methanol (50 mL) and dichloromethane (25 mL). The filtrate was concentrated under vacuum. The residue obtained was dissolved in EtOAc (50 mL) and washed with 1% aqueous KOH solution (25 mL). The organic layer was dried over anhydrous sodium sulfate and the solvent was removed to dryness in vacuo to give 486 mg of crude N-[2-(4-aminobenzenesulfonylamino) -phenyl]-2-methoxy-5-trifluoro methanesulfonyl-benzenesulfonamide. LC: Tr 1.09 min; MS: 566.7 (M+1)+.

Workup

  1. customthe resulting reaction mixture
  2. filtrationThe reaction mixture was filtered through a short pad of Celite
  3. washthe pad was washed with methanol (50 mL) and dichloromethane (25 mL)
  4. concentrationThe filtrate was concentrated under vacuum
  5. customThe residue obtained
  6. washwashed with 1% aqueous KOH solution (25 mL)
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. customthe solvent was removed to dryness in vacuo

Sources & evidence

ORD record
ord-26784dd28dd7449cbdbe4ef80b5a52d2
Source dataset
uspto-grants-2009_09
Patent number
US07582673B2

Reaction notes

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