Sodium Dithionite → HCID 20378815, compound

HRID 2052122Notes

Reaction equation

HRID 2052122 reaction equation
[O-]S(S([O-])=O)=O.[Na+].[Na+].[Cl:9][CH:10]([Cl:24])[CH:11]=[CH:12][S:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[C:16]([N+:21]([O-])=O)[CH:15]=1>CO.O>[Cl:24][C:10]([Cl:9])=[CH:11][CH2:12][S:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[C:16]([NH2:21])[CH:15]=1

Participants

4

Reactant 2

HCID 24489Sodium DithioniteHCID 54092469HCID 54092469, compound

Product 1

HCID 20378815HCID 20378815, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

In 340 cc of a 1:1 (by volume) mixture of methanol-water containing 43 g of Na2S2O4 were suspended 34.4 millimols of 4-[(3,3-dichloropropenyl)-thio]-2-nitroaniline. The reduction of the nitro-group was achieved in very short times (10-15 min.) as was ascertained by thin-layer chromatography. After the reduction was completed, the methanol and part of the water were removed under vacuum thereby obtaining an oily suspension which was then extracted with chloroform. The organic extracts, after drying on anhydrous Na2SO4, and evaporation of the solvent under vacuum, yielded, with practically quantitative yields, the raw diamine (an intensely colored thick oil) which was directly used for the successive stage.

Workup

  1. customwas achieved in very short times (10-15 min.)
  2. customthe methanol and part of the water were removed under vacuum
  3. customthereby obtaining an oily suspension which
  4. extractionwas then extracted with chloroform
  5. dry with materialThe organic extracts, after drying on anhydrous Na2SO4, and evaporation of the solvent under vacuum
  6. customyielded, with practically quantitative yields

Sources & evidence

ORD record
ord-13f9fedbbfc149859a929f54f56f9b36
Source dataset
uspto-grants-1980_01
Patent number
US04182893

Reaction notes

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