Methylhydrazine → HCID 13754302, compound

HRID 231550Notes

Reaction equation

HRID 231550 reaction equation
[CH3:1][NH:2][NH2:3].[C:4]([NH:6][C:7](=[N:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:16]=1[CH:17]=[CH:18][N:19]=[C:20]2[N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)SC)#[N:5]>CN(C=O)C>[NH2:5][C:4]1[N:6]=[C:7]([NH:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:24]=[CH:23][CH:22]=[C:21]3[C:16]=2[CH:17]=[CH:18][N:19]=[C:20]3[N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[N:2]([CH3:1])[N:3]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 13754289HCID 13754289, compound

Product 1

HCID 13754302HCID 13754302, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

Methyl hydrazine (7.3 g) is added to a stirred suspension of 1-cyano-2-methyl-3-[3-(1-morpholino-5-isoquinolyloxy)propyl]pseudothiourea (11.56 g) in DMF (91.5 ml). The reaction mixture is stirred at 40° C. under nitrogen for 24 hrs and evaporated in vacuo resulting in a red oil which partially crystallizes on standing. The residue is dissolved in boiling acetonitrile (150 ml) and the hot solution treated with Darco G-60, filtered through Celite, concentrated and cooled. The precipitate is collected, washed with acetonitrile and dried in vacuo at elevated temperature. The dried precipitate is recrystallized from absolute ethanol, dried in vacuo at 75° C. affording the desired product as a powder, M.P. 178°-180° C. Elemental analysis indicates the product as a 1/4 hydrate.

Workup

  1. customevaporated in vacuo
  2. customresulting in a red oil which
  3. custompartially crystallizes
  4. dissolutionThe residue is dissolved
  5. additionthe hot solution treated with Darco G-60
  6. filtrationfiltered through Celite
  7. concentrationconcentrated
  8. temperaturecooled
  9. customThe precipitate is collected
  10. washwashed with acetonitrile
  11. customdried in vacuo at elevated temperature
  12. customThe dried precipitate is recrystallized from absolute ethanol
  13. customdried in vacuo at 75° C.

Sources & evidence

ORD record
ord-274c3a6e856b47f89d210ba75fdb361f
Source dataset
uspto-grants-1989_07
Patent number
US04847264

Reaction notes

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