Hydrochloric Acid → Ranisen

HRID 434782Notes

Reaction equation

HRID 434782 reaction equation
O1CCO[CH:2]1[C:6]1[O:10][C:9]([CH2:11][S:12][CH2:13][CH2:14][NH:15][C:16]([NH:21][CH3:22])=[CH:17][N+:18]([O-:20])=[O:19])=[CH:8][CH:7]=1.Cl.[CH3:24][NH:25][CH3:26]>O1CCCC1.C(O)C.C(O)(=O)C>[CH3:24][N:25]([CH2:2][C:6]1[O:10][C:9]([CH2:11][S:12][CH2:13][CH2:14][NH:15][C:16]([NH:21][CH3:22])=[CH:17][N+:18]([O-:20])=[O:19])=[CH:8][CH:7]=1)[CH3:26]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 70483416HCID 70483416, compound

Product 1

HCID 5039Ranisen

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of N-[2-[[5-(1,3-dioxolan-2-yl)-2-furanylmethyl]thio]ethyl]-N'-methyl-2-nitro-1,1-ethenediamine (0.12 g) in tetrahydrofuran (1 ml) at room temperature was added 2 N hydrochloric acid (0.4 ml). After 20 min., a mixture of dimethylamine in ethanol (33%) (1 ml) and acetic acid (5 ml), evaporated to remove the ethanol, was added. The mixture was allowed to stand at room temperature for 20 min., then cooled in an ice bath. To the stirred solution was added sodium borohydride (0.4 g) portionwise during 5 min. After 10 min, acetic acid (1 ml) was added and the solution heated on a steam bath for 15 min. Tetrahydrofuran (30 ml) and excess of sodium carbonate were added and the mixture heated to boiling then cooled to room temperature. After 1 h, the mixture was filtered and the combined filtrate and washings evaporated in vacuo to give an oily residue which was extracted with hot ethyl acetate (25 ml). The extract was evaporated in vacuo to give an oily residue consisting of the title compound (0.06 g).

Workup

  1. customevaporated
  2. customto remove the ethanol
  3. additionwas added
  4. waitto stand at room temperature for 20 min.
  5. temperaturecooled in an ice bath
  6. additionTo the stirred solution was added sodium borohydride (0.4 g) portionwise during 5 min
  7. waitAfter 10 min
  8. additionacetic acid (1 ml) was added
  9. temperaturethe solution heated on a steam bath for 15 min
  10. additionTetrahydrofuran (30 ml) and excess of sodium carbonate were added
  11. temperaturethe mixture heated
  12. waitAfter 1 h
  13. filtrationthe mixture was filtered
  14. customthe combined filtrate and washings evaporated in vacuo
  15. customto give an oily residue which
  16. extractionwas extracted with hot ethyl acetate (25 ml)
  17. customThe extract was evaporated in vacuo
  18. customto give an oily residue

Sources & evidence

ORD record
ord-8d24263e78b844e59ad517c5eb56f493
Source dataset
uspto-grants-1983_08
Patent number
US04399294

Reaction notes

Loading…