Propargylamine → HCID 178457562, compound

HRID 544344Notes

Reaction equation

HRID 544344 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]>C(#N)C>[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, compoundYield 116.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of N-cyano-N'-{2-[(4-methyl-5-imidazolyl)methylthio]ethyl}-S-methyl isothiourea (3.00 g, 0.0111 mole) and propargyl amine (2.50 g, 0.045 mole) in acetonitrile (60 ml) as stirred at reflux for 65 hours, and then was heated in a stainless steel pressure vessel at 120°-130° for 38 hours. The reaction mixture was cooled, decanted from a tar, and then evaporated to leave a gum (3.57 g). This material was placed on silica gel (100-200 mesh) and eluted with a mixture of methylene chloride (97 parts) and methanol (3 parts). The product obtained from a middle fraction was crystallized by trituration under acetonitrile, and then was recrystallized from acetonitrile to yield the title compound (0.236 g; 7.7%); m.p. 146°-149.5°.

Workup

  1. temperatureat reflux for 65 hours
  2. temperaturewas heated in a stainless steel pressure vessel at 120°-130° for 38 hours
  3. temperatureThe reaction mixture was cooled
  4. customdecanted from a tar
  5. customevaporated

Sources & evidence

ORD record
ord-c416bf9d832f40ec990391cabaeb4b17
Source dataset
uspto-grants-1984_05
Patent number
USRE031588

Reaction notes

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