1,1-Bis(methylthio)-2-nitroethylene → HCID 70537224, compound

HRID 224640Notes

Reaction equation

HRID 224640 reaction equation
[CH3:1][S:2][C:3](SC)=[CH:4][N+:5]([O-:7])=[O:6].[NH2:10][CH2:11][CH2:12][CH2:13][O:14][CH2:15][C:16]1[O:20][C:19]([CH2:21][N:22]([CH3:24])[CH3:23])=[CH:18][CH:17]=1>O1CCOCC1>[CH3:24][N:22]([CH3:23])[CH2:21][C:19]1[O:20][C:16]([CH2:15][O:14][CH2:13][CH2:12][CH2:11][NH:10][C:3]([S:2][CH3:1])=[CH:4][N+:5]([O-:7])=[O:6])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 19750881HCID 19750881, compound

Product 1

HCID 70537224HCID 70537224, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 1,1-bis(methylthio)-2-nitroethene (3.96 g) in dry dioxan (25 ml) at 70° was added dropwise 5-[(3-aminopropoxy)methyl]-N,N-dimethyl-2-furanmethanamine (1.27 g). After 1 hr the reaction was allowed to cool and the solid which separated was filtered. The filtrate and washings were combined and evaporated to dryness, a solution of succinic acid (1 g) in water (25 ml) added to the residue and the suspension filtered. The filtrate was washed with ethyl acetate (2×40 ml) then evaporated to 10 ml. The solution was basified with sodium carbonate and the oily precipitate which separated was extracted into ethyl acetate (3×25 ml). The combined extracts were dried (anhyd. sodium carbonate), the suspension filtered and evaporated to dryness to yield the title compound (1.34 g) as a brown oil.

Workup

  1. temperatureto cool
  2. customthe solid which separated
  3. filtrationwas filtered
  4. customevaporated to dryness
  5. additiona solution of succinic acid (1 g) in water (25 ml) added to the residue
  6. filtrationthe suspension filtered
  7. washThe filtrate was washed with ethyl acetate (2×40 ml)
  8. customthen evaporated to 10 ml
  9. customthe oily precipitate which separated
  10. extractionwas extracted into ethyl acetate (3×25 ml)
  11. dry with materialThe combined extracts were dried (anhyd. sodium carbonate)
  12. filtrationthe suspension filtered
  13. customevaporated to dryness

Sources & evidence

ORD record
ord-036a7d15d646405cacff7cae9e5680a4
Source dataset
uspto-grants-1980_11
Patent number
US04233302

Reaction notes

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