Potassium Hydroxide → Ranisen

HRID 1648824Notes

Reaction equation

HRID 1648824 reaction equation
C(O)(=O)/C=C\C(O)=O.[CH3:9][N:10]([CH2:12][C:13]1[O:17][C:16]([CH2:18][S:19][C:20](=N)N)=[CH:15][CH:14]=1)[CH3:11].ClC[CH2:25][NH:26][C:27]([NH:32][CH3:33])=[CH:28][N+:29]([O-:31])=[O:30].[OH-].[K+]>O.CO.CC(C)=O>[CH3:11][N:10]([CH2:12][C:13]1[O:17][C:16]([CH2:18][S:19][CH2:20][CH2:25][NH:26][C:27]([NH:32][CH3:33])=[CH:28][N+:29]([O-:31])=[O:30])=[CH:15][CH:14]=1)[CH3:9]

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 70486838HCID 70486838, compoundHCID 71421354N~1~-(2-Chloroethyl)-N'~1~-methyl-2-nitroethene-1,1-diamine

Product 1

HCID 5039RanisenYield 19.6%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a stirred solution of 1-[[5-[(Dimethylamino)methyl]-2-furanylmethyl]thio]methanimidamide maleate (1:2) (2.23 g) and N-(2-chloroethyl)-N'-methyl-2-nitro-1,1-ethenediamine (1.08 g) in water (20 ml) at 45° under an atmosphere of nitrogen was added a solution of potassium hydroxide (1.68 g) in water (3 ml). After 40 hr. at room temperature the solution was extracted with ether (2×50 ml) and the aqueous phase evaporated in vacuo. Tetrahydrofuran (70 ml), decolourising charcoal and an excess of anhydrous sodium carbonate were added to the residue and the mixture refluxed for 30 mins. After 3 hours the mixture was filtered and the filtrate evaporated in vacuo to give a semi-solid which was dissolved in a mixture of methanol and acetone and chromatographed (silica;methanol:acetone 1:1). The appropriate eluate was evaporated in vacuo to give the title compound as an oil (0.37 g), a portion of which was crystallised from 4-methylpentan-2-one, m.p. 68°-70° which was not depressed on admixture with a sample prepared according to the method of Example 15 in British Patent No. 1,565,966.

Workup

  1. extractionat room temperature the solution was extracted with ether (2×50 ml)
  2. customthe aqueous phase evaporated in vacuo
  3. additionan excess of anhydrous sodium carbonate were added to the residue
  4. temperaturethe mixture refluxed for 30 mins
  5. filtrationAfter 3 hours the mixture was filtered
  6. customthe filtrate evaporated in vacuo
  7. customto give a semi-solid which
  8. customchromatographed (silica;methanol:acetone 1:1)
  9. customThe appropriate eluate was evaporated in vacuo

Sources & evidence

ORD record
ord-eca3a30a43a54dfaa0fb82bf5edba3d5
Source dataset
uspto-grants-1983_11
Patent number
US04413135

Reaction notes

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