Methylhydrazine → HCID 54199411, compound

HRID 2058720Notes

Reaction equation

HRID 2058720 reaction equation
[CH3:1][NH:2][NH2:3].CN(C)C=O.[C:9]([N:11]=[C:12](SC)[NH:13][CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][N:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)[CH:19]=1)#[N:10]>C1(C)C=CC=CC=1>[CH3:1][N:2]1[C:12]([NH:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][N:25]3[CH2:26][CH2:27][CH2:28][CH2:29]3)[CH:19]=2)=[N:11][C:9]([NH2:10])=[N:3]1

Participants

5

Reactant 3

HCID 6061MethylhydrazineHCID 6228DimethylformamideHCID 178503919HCID 178503919, compound

Product 1

HCID 54199411HCID 54199411, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl hydrazine (6.9 g) and dry dimethylformamide (10.95 g) were heated at reflux in toluene for 1 hr. N'-Cyano-N-[3-[3-(1-pyrrolidinylmethyl)phenoxy]propyl]carbamimidothioic acid, methyl ester (10 g) was then added and the mixture heated at reflux for 5 hr. Evaporation of the solvent gave the title compound as a yellow oil which was converted to the fumarate salt in ethanol. The title compound was regenerated as the free base with aqueous sodium carbonate, and extracted into ethyl acetate. Evaporation of the solvent and trituration of the residue with light petroleum (b.p. 60°-80°) gave the title compound as a white solid (3.4 g) m.p. 95°-95.5°. TLC silica; methanol:0.88 ammonia (80:1) single spot Rf 0.5.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 5 hr
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-695cd384d8ac4d76bc858592a67c464a
Source dataset
uspto-grants-1982_03
Patent number
US04318913

Reaction notes

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