Hydrochloric Acid → Ranisen

HRID 434781Notes

Reaction equation

HRID 434781 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].Cl.CNC.[BH4-].[Na+]>O.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

8

Reactant 5

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 10473Dimethylamine, hydrochlorideHCID 4311764Sodium borohydrideHCID 70483416HCID 70483416, compound

Product 1

HCID 5039RanisenYield 21.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of N-[2-[[5-(1,3-dioxolan-2-yl)-2-furanylmethyl]thio]ethyl]-N'-methyl-2-nitro-1,1-ethenediamine (2.21 g) and dimethylamine hydrochloride (20 g) in water (5 ml) was added 2 N hydrochloric acid (5 ml). After 10 min, dimethylamine (33% in ethanol) (2 ml) was added, the solution cooled to 18° and sodium borohydride (1 g) added portionwise. The suspension was acidified with acetic acid (2.5 ml) and after 15 mins was heated at 60° for 15 mins. The suspension was evaporated to low bulk and an excess of anhydrous sodium carbonate and tetrahydrofuran (100 ml) added. The suspension was refluxed for 2 hours and after 2 hours at room temperature was filtered and the filtrate evaporated in vacuo. The oily residue was chromatographed (silica/methanol) and the appropriate eluate evaporated in vacuo to give the title compound (0.45 g) which was crystallised from methyl isobutyl ketone, m.p. 64°-67° .

Workup

  1. temperaturethe solution cooled to 18°
  2. temperaturewas heated at 60° for 15 mins
  3. customThe suspension was evaporated to low bulk
  4. additionan excess of anhydrous sodium carbonate and tetrahydrofuran (100 ml) added
  5. filtrationwas filtered
  6. customthe filtrate evaporated in vacuo
  7. customThe oily residue was chromatographed (silica/methanol)
  8. customthe appropriate eluate evaporated in vacuo

Sources & evidence

ORD record
ord-2b82f27ec2b24bcbbcf39ec92af0f908
Source dataset
uspto-grants-1983_08
Patent number
US04399294

Reaction notes

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