Propargylamine → HCID 73683993, compound

HRID 1577922Notes

Reaction equation

HRID 1577922 reaction equation
[N+:1]([CH:4]=[C:5](SC)[NH:6][CH2:7][CH2:8][S:9][CH2:10][C:11]1[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][N:12]=1)([O-:3])=[O:2].[CH2:20]([NH2:23])[C:21]#[CH:22]>C(#N)C>[N+:1]([CH:4]=[C:5]([NH:23][CH2:20][C:21]#[CH:22])[NH:6][CH2:7][CH2:8][S:9][CH2:10][C:11]1[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][N:12]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 239041PropargylamineHCID 70571919HCID 70571919, compound

Product 1

HCID 73683993HCID 73683993, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-nitro-2-methylthio-2-{2-[(3-chloro-2-pyridyl)methylthio]ethylamino}ethylene (0.61 g; 1.91 mmoles) [prepared according to the procedure described in U.S. Pat. No. 4,024,260] and propargylamine (1.72 g; 31.2 mmoles) in acetonitrile (15 ml) was stirred and heated to reflux temperature under a positive pressure of nitrogen for 7 hours then allowed to stand at ambient temperature for 16 hours. The reaction mixture was filtered and 346 mg of product collected. Recrystallization from methanol with activated carbon treatment gave the title compound; mp 171°-171.5°.

Workup

  1. temperatureheated
  2. temperatureto reflux temperature under a positive pressure of nitrogen for 7 hours
  3. filtrationThe reaction mixture was filtered
  4. custom346 mg of product collected
  5. customRecrystallization from methanol with activated carbon treatment

Sources & evidence

ORD record
ord-2a98bcf43465469390909240de50f066
Source dataset
uspto-grants-1981_09
Patent number
US04289876

Reaction notes

Loading…