Potassium Carbonate → Ranisen

HRID 1648822Notes

Reaction equation

HRID 1648822 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].C(=O)([O-])[O-].[K+].[K+]>O.O1CCCC1>[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

6

Reactant 3

HCID 11430Potassium CarbonateHCID 70486838HCID 70486838, compoundHCID 71421354N~1~-(2-Chloroethyl)-N'~1~-methyl-2-nitroethene-1,1-diamine

Product 1

HCID 5039RanisenYield 19%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-[[[5-[(dimethylamino)methyl]-2-furanyl]-methyl]thio]methanimidamide maleate (1:2) (2.23 g), N-(2-chloroethyl)-N'-methyl-2-nitro-1,1-ethenediamine (0.9 g) and potassium carbonate (3.46 g) in water (10 ml) and tetrahydrofuran (10 ml) was stirred under nitrogen at room temperature for 5 days. The suspension was evaporated in vacuo; the residue suspended in water (50 ml) and extracted with ether (2×40 ml). The aqueous fraction was evaporated in vacuo and magnesium sulphate and tetrahhydrofuran (100 ml) added. After 18 hours, the mixture was filtered and the filtrate evaporated to give a semi-solid which was chromatographed (silica/methanol). The appropriate eluate was evaporated in vacuo to give the title compound (0.3 g), which had an n.m.r. identical to that of the product according to Example 1 above.

Workup

  1. customThe suspension was evaporated in vacuo
  2. extractionextracted with ether (2×40 ml)
  3. customThe aqueous fraction was evaporated in vacuo and magnesium sulphate and tetrahhydrofuran (100 ml)
  4. additionadded
  5. waitAfter 18 hours
  6. filtrationthe mixture was filtered
  7. customthe filtrate evaporated
  8. customto give a semi-solid which
  9. customwas chromatographed (silica/methanol)
  10. customThe appropriate eluate was evaporated in vacuo

Sources & evidence

ORD record
ord-a45c1f3dc44849c4a1d96b059fb982f2
Source dataset
uspto-grants-1983_11
Patent number
US04413135

Reaction notes

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