Potassium Hydroxide → Ranisen

HRID 615257Notes

Reaction equation

HRID 615257 reaction equation
C(O)(=O)C(O)=O.[CH3:7][N:8]([CH2:10][C:11]1[O:15][C:14]([CH2:16][SH:17])=[CH:13][CH:12]=1)[CH3:9].Cl[CH2:19][CH2:20][NH:21][C:22]([NH:27][CH3:28])=[CH:23][N+:24]([O-:26])=[O:25].[OH-].[K+]>O>[CH3:9][N:8]([CH2:10][C:11]1[O:15][C:14]([CH2:16][S:17][CH2:19][CH2:20][NH:21][C:22]([NH:27][CH3:28])=[CH:23][N+:24]([O-:26])=[O:25])=[CH:13][CH:12]=1)[CH3:7]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 12888901HCID 12888901, compoundHCID 71421354N~1~-(2-Chloroethyl)-N'~1~-methyl-2-nitroethene-1,1-diamine

Product 1

HCID 5039RanisenYield 45.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred mixture of 5-[(dimethylamino)methyl]-2-furanmethane-thiol oxalate (1:1) (1.31 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 (1.04 g) in water (3 ml). The solution was stirred at 45° for 2.5 hr. and at room temperature for 15 hr. The solution was then evaporated in vacuo, the residue dissolved in water and a stream of air passed into the mixture for 15 mins. The mixture was extracted with ether (2×15 ml) and the aqueous fraction evaporated in vacuo. To the residue was added tetrahydrofuran (70 ml), an excess of anhydrous sodium carbonate, and decolourising charcoal. After 1 hr the mixture was filtered, the filtrate evaporated in vacuo and the oily residue dissolved in 4-methyl-pentan-2-one (8 ml). The solid which separated was filtered and washed with 4-methylpentan-2-one to give the title compound (0.72 g), m.p. 63°-66°, which was not depressed on admixture with a sample prepared according to the method of Example 15 in British Patent Specification No. 1565966.

Workup

  1. waitand at room temperature for 15 hr
  2. customThe solution was then evaporated in vacuo
  3. dissolutionthe residue dissolved in water
  4. waita stream of air passed into the mixture for 15 mins
  5. extractionThe mixture was extracted with ether (2×15 ml)
  6. customthe aqueous fraction evaporated in vacuo
  7. additionTo the residue was added tetrahydrofuran (70 ml)
  8. filtrationAfter 1 hr the mixture was filtered
  9. customthe filtrate evaporated in vacuo
  10. dissolutionthe oily residue dissolved in 4-methyl-pentan-2-one (8 ml)
  11. customThe solid which separated
  12. filtrationwas filtered
  13. washwashed with 4-methylpentan-2-one

Sources & evidence

ORD record
ord-d9caf3b974634a629775a3010935ea15
Source dataset
uspto-grants-1985_02
Patent number
US04497961

Reaction notes

Loading…