Methylhydrazine → HCID 54199411, compound

HRID 35053Notes

Reaction equation

HRID 35053 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 adde 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-be0e956cb0ac4935bdca9d449076a46a
Source dataset
uspto-grants-1988_08
Patent number
US04764612

Reaction notes

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