Sodium Pyrosulfite → 4-amino-N-[2-(2,4-dichlorophenoxy)phenyl]benzenesulfonamide

HRID 746744Notes

Reaction equation

HRID 746744 reaction equation
[Cl:1][C:2]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=1)(=[O:14])=[O:13].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>CO.C(Cl)Cl.O>[NH2:21][C:18]1[CH:17]=[CH:16][C:15]([S:12]([NH:11][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]2[CH:24]=[CH:25][C:26]([Cl:28])=[CH:27][C:2]=2[Cl:1])(=[O:13])=[O:14])=[CH:20][CH:19]=1

Participants

6

Reactant 2

HCID 656671Sodium PyrosulfiteHCID 69311367N-[2-(2,4-dichlorophenoxy)phenyl]-4-nitrobenzenesulfonamide

Product 1

HCID 27307034-amino-N-[2-(2,4-dichlorophenoxy)phenyl]benzenesulfonamide

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound of Step 1 (2.12 g) in methanol (50 mL) and CH2Cl2 (50 mL) was added a solution of sodium metabisulfite (2.52 g) in water (50 mL) at room temperature. After 3 hrs the methanol was evaporated in vacuo. The residue was partitioned between sat. aq. Na2CO3 and EtOAc, Dried over MgSO4 and evaporated in vacuo. The resulting orange solid was absorbed onto silica gel (10 g) and purified by flash chromatography SiO2, 0-50% EtOAc Hexanes gradient elution to afford the title compound as a yellow solid. C18H14Cl2N2O3S MH+ requires 409.0175 found 409.0162.

Workup

  1. customAfter 3 hrs the methanol was evaporated in vacuo
  2. customThe residue was partitioned between sat. aq. Na2CO3 and EtOAc
  3. dry with materialDried over MgSO4
  4. customevaporated in vacuo
  5. customThe resulting orange solid was absorbed onto silica gel (10 g)
  6. custompurified by flash chromatography SiO2, 0-50% EtOAc Hexanes gradient elution

Sources & evidence

ORD record
ord-f0d08da2de024e3f99d3700a6d5fd585
Source dataset
uspto-grants-2008_07
Patent number
US07393873B2

Reaction notes

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