Propargylamine → HCID 178457562, compound

HRID 544348Notes

Reaction equation

HRID 544348 reaction equation
[C:1]([NH:3][C:4](=[N:7][CH2:8][CH2:9][S:10][CH2:11][C:12]1[NH:16][CH:15]=[N:14][C:13]=1[CH3:17])SC)#[N:2].[CH2:18]([NH2:21])[C:19]#[CH:20]>CO>[C:1]([NH:3][C:4]([NH:7][CH2:8][CH2:9][S:10][CH2:11][C:12]1[NH:16][CH:15]=[N:14][C:13]=1[CH3:17])=[N:21][CH2:18][C:19]#[CH:20])#[N:2]

Participants

4

Reactant 2

HCID 239041PropargylamineHCID 178503877HCID 178503877, compound

Product 1

HCID 178457562HCID 178457562, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-cyano-N'-{2-[(4-methyl-5-imidazolyl)methylthio]ethyl}-S-methylisothiourea (100 g; 0.371 mole) and distilled propargylamine (150 ml; 2.44 moles) in methanol (500 ml) was stirred at reflux under a positive pressure nitrogen atmosphere (nitrogen sweep) for 22 hours. The reaction mixture was cooled, and the solvent and excess amine were removed by evaporation to leave an amber oil that readily crystallized. The crude product was triturated under isopropanol (250 ml), cooled at 0° for 2 hours and collected by filtration. The filter cake was washed with cold isopropanol and dried in vacuo over P2O5 for 16 hours. The dried title product was a near-white dense solid; yield 73.5 gm (71.7%) m.p. 147°-149°.

Workup

  1. temperatureat reflux under a positive pressure nitrogen atmosphere (nitrogen sweep) for 22 hours
  2. temperatureThe reaction mixture was cooled
  3. customthe solvent and excess amine were removed by evaporation
  4. customto leave an amber oil
  5. customthat readily crystallized
  6. customThe crude product was triturated under isopropanol (250 ml)
  7. temperaturecooled at 0° for 2 hours
  8. filtrationcollected by filtration
  9. washThe filter cake was washed with cold isopropanol
  10. dry with materialdried in vacuo over P2O5 for 16 hours
  11. dry with materialThe dried title product

Sources & evidence

ORD record
ord-e4427fc0f45c402db0a60e4cbfa5a86c
Source dataset
uspto-grants-1984_05
Patent number
USRE031588

Reaction notes

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