HCID 86622289, compound → HCID 86622288, compound

HRID 1639557Notes

Reaction equation

HRID 1639557 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[S:9]([O:12][C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[C:15]([N+:20]([O-])=O)[CH:14]=1)(=[O:11])=[O:10]>CO.C(O)(=O)C.[Fe]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[S:9]([O:12][C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[C:15]([NH2:20])[CH:14]=1)(=[O:11])=[O:10]

Participants

5

Reactant 1

HCID 86622289HCID 86622289, compound

Product 1

HCID 86622288HCID 86622288, compoundYield 49%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 2 g of 4-amino-3-nitrophenyl 2,6-dichlorobenzenesulfonate in 85 cm3 of methanol and 33 cm3 of pure acetic acid are added 2.25 g of iron powder. The reaction medium is refluxed for three hours. The insoluble material is filtered off and washed with three times 10 cm3 of preheated methanol. The filtrate is evaporated to dryness under reduced pressure (2 kPa) at a bath temperature of 50° C. The residue is taken up in 50 cm3 of water and then brought to pH 8-9 with sodium hydrogen carbonate and extracted with five times 80 cm3 of dichloromethane. The combined organic phases are dried over magnesium sulfate, filtered and evaporated to dryness under reduced pressure (2 kPa). After flash chromatography on a column of silica [eluent: dichloromethane/methanol (98/2 by volume)], 900 mg of 3,4-diaminophenyl 2,6-dichlorobenzenesulfonate are obtained in the form of orange crystals, the characteristics of which are as follows:

Workup

  1. temperatureThe reaction medium is refluxed for three hours
  2. filtrationThe insoluble material is filtered off
  3. washwashed with three times 10 cm3 of preheated methanol
  4. customThe filtrate is evaporated to dryness under reduced pressure (2 kPa) at a bath temperature of 50° C
  5. extractionextracted with five times 80 cm3 of dichloromethane
  6. dry with materialThe combined organic phases are dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness under reduced pressure (2 kPa)

Sources & evidence

ORD record
ord-43418cfb4d51452ba021dc4d71517189
Source dataset
uspto-grants-2012_02
Patent number
US08110571B2

Reaction notes

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