Propargylamine → HCID 178457543, compound

HRID 27384Notes

Reaction equation

HRID 27384 reaction equation
[C:1]([C:3]([C:18]#[N:19])=[C:4](SC)[NH:5][CH2:6][CH2:7][S:8][CH2:9][C:10]1[NH:14][CH:13]=[N:12][C:11]=1[CH3:15])#[N:2].[CH2:20]([NH2:23])[C:21]#[CH:22]>C(#N)C>[C:1]([C:3]([C:18]#[N:19])=[C:4]([NH:23][CH2:20][C:21]#[CH:22])[NH:5][CH2:6][CH2:7][S:8][CH2:9][C:10]1[NH:14][CH:13]=[N:12][C:11]=1[CH3:15])#[N:2]

Participants

4

Reactant 2

HCID 239041PropargylamineHCID 178503874HCID 178503874, compound

Product 1

HCID 178457543HCID 178457543, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of the product of Step A (4.3 g, 14.7 mmole) and propargylamine (8.6 ml) in acetonitrile (43 ml) was stirred at reflux temperature under a positive pressure of nitrogen for 15 hours then at room temperature for an additional 48 hours. The reaction mixture was filtered to remove by-product and the filtrate was evaporated under reduced pressure. The residual gum was placed on silica gel and chromatographed by gradient elution using methylene chloride-methanol. The appropriate fractions were combined and the product recrystallized from acetonitrile to give the title compound; mp 112.5°-115°.

Workup

  1. temperatureat reflux temperature under a positive pressure of nitrogen for 15 hours
  2. filtrationThe reaction mixture was filtered
  3. customto remove by-product
  4. customthe filtrate was evaporated under reduced pressure
  5. customchromatographed by gradient elution
  6. customthe product recrystallized from acetonitrile

Sources & evidence

ORD record
ord-8a55e55f46544409a4963e8f9b9d7919
Source dataset
uspto-grants-1980_09
Patent number
US04221737

Reaction notes

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