Acetonitrile → HCID 178509163, compound

HRID 1380518Notes

Reaction equation

HRID 1380518 reaction equation
[O:1]([CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CSC(SC)=[N:19][C:20]#[N:21].O.[NH2:25]N.[C:27](#[N:29])C>>[NH2:19][C:20]1[NH:21][C:27]([N:13]2[CH2:12][CH2:11][N:10]([CH2:9][CH2:8][O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:15][CH2:14]2)=[N:29][N:25]=1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 24654Hydrazine hydrate (1:1)HCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 2331871-(2-Phenoxyethyl)piperazine

Product 1

HCID 178509163HCID 178509163, compound

Procedure

In the manner of Example 3 a mixture of 10.3 g (0.05 moles) of 1-[2-phenoxyethyl]piperazine and 7.3 g (0.05 moles) of dimethyl cyanodithioiminocarbonate in 250 ml of acetonitrile was refluxed for 3 hours. After cooling, 2.8 ml (0.056 moles) of hydrazine hydrate was added and the mixture was refluxed for 45 minutes. The mixture was cooled, filtered through diatomaceous earth and the filtrate was evaporated to a paste. The product was crystallized from ethanol/ether/hexane, collected and washed with ether and gave 5.3 g of colorless crystals, mp 131°-133° C.

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperatureAfter cooling
  3. temperaturethe mixture was refluxed for 45 minutes
  4. temperatureThe mixture was cooled
  5. filtrationfiltered through diatomaceous earth
  6. customthe filtrate was evaporated to a paste
  7. customThe product was crystallized from ethanol/ether/hexane
  8. customcollected
  9. washwashed with ether

Sources & evidence

ORD record
ord-0c592fc6242142c6a9a2d3228d1b756a
Source dataset
uspto-grants-1986_04
Patent number
US04582833

Reaction notes

Loading…