Potassium Carbonate → Ranisen

HRID 1648821Notes

Reaction equation

HRID 1648821 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([NH:10][CH3:11])=[CH:6][N+:7]([O-:9])=[O:8].C(O)(=O)C(O)=O.[CH3:18][N:19]([CH2:21][C:22]1[O:26][C:25]([CH2:27][SH:28])=[CH:24][CH:23]=1)[CH3:20].C(=O)([O-])[O-].[K+].[K+]>O.O1CCCC1>[CH3:20][N:19]([CH2:21][C:22]1[O:26][C:25]([CH2:27][S:28][CH2:2][CH2:3][NH:4][C:5]([NH:10][CH3:11])=[CH:6][N+:7]([O-:9])=[O:8])=[CH:24][CH:23]=1)[CH3:18]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 12888901HCID 12888901, compoundHCID 71421354N~1~-(2-Chloroethyl)-N'~1~-methyl-2-nitroethene-1,1-diamine

Product 1

HCID 5039RanisenYield 63.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-(2-chloroethyl)-N'-methyl-2-nitro-1,1-ethenediamine (0.9 g), 5-[(dimethylamino)methyl]-2-furanmethanethiol oxalate (1:1) (1.3 g) and potassium carbonate (2.7 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 mixed with water (40 ml) and the suspension extracted with ether (2×30 ml). The aqueous fraction was evaporated in vacuo and the residue evaporated with ethanol (2×10 ml). Tetrahydrofuran (20 ml), MgSO4 and decolourising charcoal were added and after 1 hour the mixture was filtered. Evaporation of the filtrate gave an oil (1 g) which was chromatographed (silica/methanol: 0.88 ammonia, 79:1). The appropriate eluate was evaporated and the oily residue (0.66 g) extracted with hot isopropyl acetate. The solid which separated was filtered to give the title compound (0.4 g), m.p. 65°-68°, 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. customThe suspension was evaporated in vacuo
  2. additionthe residue mixed with water (40 ml)
  3. extractionthe suspension extracted with ether (2×30 ml)
  4. customThe aqueous fraction was evaporated in vacuo
  5. customthe residue evaporated with ethanol (2×10 ml)
  6. additionwere added and after 1 hour the mixture
  7. filtrationwas filtered
  8. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-8be92b80d96e493c94fbd91f252d912d
Source dataset
uspto-grants-1983_11
Patent number
US04413135

Reaction notes

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