Sodium Dithionite → HCID 10167977, compound

HRID 892288Notes

Reaction equation

HRID 892288 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:20]=[C:21]([Br:32])[C:22]=1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([Br:31])[CH:26]=1)[C:5]([NH:7][S:8]([C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=1)(=[O:10])=[O:9])=[O:6].S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(O)C>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([S:8]([NH:7][C:5](=[O:6])[C:4]2[CH:3]=[C:2]([Br:1])[C:22]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([Br:31])[CH:26]=3)=[C:21]([Br:32])[CH:20]=2)(=[O:9])=[O:10])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 24489Sodium DithioniteHCID 10211643HCID 10211643, compound

Product 1

HCID 10167977HCID 10167977, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of N-[3,5-dibromo-4-(3-bromobenzyloxy)benzoyl]-4-nitrobenzenesulphonamide (0.25 mmol), prepared as described in Example 33, in ethanol (95%, 25 mL), sodium dithionite (1.26 mmol) was added and the reaction mixture stirred over night at 70° C. The reaction mixture was allowed to reach room temperature and then evaporated in vacuo. The residue was diluted with ethyl acetate and washed with an aqueous solution of sodium hydrogencarbonate (saturated). The organic phase was dried over magnesium sulphate and concentrated in vacuo. The residue was purified on column (silica gel, chloroform/methanol 17:3) and further purified by semi-preparative HPLC (column and eluents as described for Examples 27, 28 an 30) to give 30 mg (20%) of 4-amino-N-[3,5-dibromo-4-(3-bromobenzyloxy)-benzoyl]benzenesulphonamide.

Workup

  1. customto reach room temperature
  2. customevaporated in vacuo
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with an aqueous solution of sodium hydrogencarbonate (saturated)
  5. dry with materialThe organic phase was dried over magnesium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified on column (silica gel, chloroform/methanol 17:3)
  8. customfurther purified by semi-preparative HPLC (column and eluents

Sources & evidence

ORD record
ord-b2c0b67c86a147a8852aec5ce2258d32
Source dataset
uspto-grants-2006_02
Patent number
US07005538B1

Reaction notes

Loading…