Methyl Isobutyl Ketone → Ranisen

HRID 426490Notes

Reaction equation

HRID 426490 reaction equation
[CH3:1][NH:2][C:3](SC)=[CH:4][N+:5]([O-:7])=[O:6].[CH3:10][N:11]([CH2:13][C:14]1[O:18][C:17]([CH2:19][S:20][CH2:21][CH2:22][NH2:23])=[CH:16][CH:15]=1)[CH3:12].CC(C)CC(=O)C>O>[CH3:12][N:11]([CH2:13][C:14]1[O:18][C:17]([CH2:19][S:20][CH2:21][CH2:22][NH:23][C:3]([NH:2][CH3:1])=[CH:4][N+:5]([O-:7])=[O:6])=[CH:16][CH:15]=1)[CH3:10]

Participants

5

Reactant 3

HCID 7909Methyl Isobutyl KetoneHCID 1235491-Methylthio-1-methylamino-2-nitroethyleneHCID 1622035-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamine

Product 1

HCID 5039Ranisen

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-Methyl-1-(methylthio)-2-nitroetheneamine (230 g) in water (400 ml) was stirred and heated at 45°-50°. 2-[[[5-(Dimethylamino)methyl-2-furanyl]methyl]thio]ethanamine (321 g) was added dropwise over 4 hr and the resultant solution stirred for a further 31/2 hr. The solution was then heated at reflux for 1/2 hr, cooled to 70° and 4-methylpentan-2-one (2 liters) added. The water was removed by azeotropic distillation under reduced pressure (260 torr) and the resultant solution treated with charcoal (10 g) at 50°. The solution was filtered and cooled to 10°. N-[2-[[[5-(dimethylamino)methyl-2-furanyl]methyl]thio]ethyl]-N'-methyl-2-nitro-1,1-ethenediamine (380 g) was filtered off and dried m.p. 69°-70°.

Workup

  1. temperatureheated at 45°-50°
  2. temperatureThe solution was then heated
  3. temperatureat reflux for 1/2 hr
  4. temperaturecooled to 70°
  5. customThe water was removed by azeotropic distillation under reduced pressure (260 torr)
  6. additionthe resultant solution treated with charcoal (10 g) at 50°
  7. filtrationThe solution was filtered
  8. temperaturecooled to 10°
  9. filtrationN-[2-[[[5-(dimethylamino)methyl-2-furanyl]methyl]thio]ethyl]-N'-methyl-2-nitro-1,1-ethenediamine (380 g) was filtered off
  10. customdried m.p. 69°-70°

Sources & evidence

ORD record
ord-b51d17f6cb084d5abfc85a770b214beb
Source dataset
uspto-grants-1979_10
Patent number
US04169855

Reaction notes

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