Sodium Dithionite → HCID 19100719, compound

HRID 1974967Notes

Reaction equation

HRID 1974967 reaction equation
[C:1]([NH:8][C:9]1[S:10][C:11]([CH:17]([CH3:19])[CH3:18])=[CH:12][C:13]=1[N+:14]([O-])=O)([C:3](OCC)=[O:4])=[O:2].S(S([O-])=O)([O-])=O.[Na+].[Na+]>O1CCOCC1.O>[CH:17]([C:11]1[S:10][C:9]2[NH:8][C:1](=[O:2])[C:3](=[O:4])[NH:14][C:13]=2[CH:12]=1)([CH3:19])[CH3:18]

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 19100755HCID 19100755, compound

Product 1

HCID 19100719HCID 19100719, compoundYield 8.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

2-Ethoxalylamino-5-isopropyl-3-nitrothiophene (i g, 3.5 mmol) was dissolved in 10 ml of dioxane at 50° C., 6 ml of water was added, and the solution was treated with 12.2 g (70 mmol) of sodium dithionite dissolved in 50 ml of warm water (50° C.) over a period of 30 minutes. The mixture was cooled and extracted with 4×25 ml of ethyl acetate. The combined organic phases were washed with water, dried (MgSO4), and concentrated to 15 ml, whereby a crop of crystals separated which was filtered off and dried to yield 65 mg (8%) of the title compound, melting over 300° C. 1H-NMR (DMSO-D6, δ): 1.2 (d, 6H) ,3.1 (m, 1H), 6.5 (s, 1H), 11.8 (broad, 1H), 12.2 (broad, 1H).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with 4×25 ml of ethyl acetate
  3. washThe combined organic phases were washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated to 15 ml, whereby a crop of crystals
  6. customseparated which
  7. filtrationwas filtered off
  8. customdried

Sources & evidence

ORD record
ord-79aa5317a9d74f939da106c0236c34bb
Source dataset
uspto-grants-1994_02
Patent number
US05284847

Reaction notes

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