Formaldehyde → Ranisen

HRID 127327Notes

Reaction equation

HRID 127327 reaction equation
[CH3:1][N:2]([CH3:9])[CH2:3][C:4]1[O:5][CH:6]=[CH:7][CH:8]=1.[CH2:10]=O.[SH:12][CH2:13][CH2:14][NH:15][C:16]([NH:21][CH3:22])=[CH:17][N+:18]([O-:20])=[O:19]>C(O)(=O)C.Cl.O.C(=O)([O-])[O-].[K+].[K+]>[CH3:1][N:2]([CH2:3][C:4]1[O:5][C:6]([CH2:10][S:12][CH2:13][CH2:14][NH:15][C:16]([NH:21][CH3:22])=[CH:17][N+:18]([O-:20])=[O:19])=[CH:7][CH:8]=1)[CH3:9]

Participants

8

Reactant 3

HCID 712FormaldehydeHCID 84478N,N-dimethyl-2-FuranmethanamineHCID 181798N-(2-Mercaptoethyl)-N'-methyl-2-nitro-1,1-ethenediamine

Product 1

HCID 5039Ranisen

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolvent2×HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 11430Potassium CarbonateSolvent

Procedure

N,N-Dimethyl-2-furanmethanamine (125 mg) was dissolved in glacial acetic acid (1 ml) and paraformaldehyde (30 mg) added. A solution of N-(2-mercaptoethyl)-N'-methyl-2-nitro-1,1-ethenediamine (354 mg) in concentrated hydrochloric acid (1 ml) and glacial acetic acid (1 ml) was added dropwise and the mixture left to stand at room temperature for 5 days. The solution was diluted with water (30 ml), saturated with potassium carbonate and extracted with ethyl acetate. The combined extracts were purified by preparative layer chromatography to give the title compound as Example 15 (89 mg).

Workup

  1. waitthe mixture left
  2. extractionextracted with ethyl acetate
  3. customThe combined extracts were purified by preparative layer chromatography

Sources & evidence

ORD record
ord-51393c636ebf477a967aec0552f04575
Source dataset
uspto-grants-1981_03
Patent number
US04255440

Reaction notes

Loading…