Pent-4-yn-1-amine → N-Cyano-N'-{2-[(4-methyl-5-imidazolyl)methylthio]ethyl}-N"-(4-pentyn-1-yl)guanidine

HRID 1763682Notes

Reaction equation

HRID 1763682 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]([NH2:23])[CH2:19][CH2:20][C:21]#[CH:22]>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:23][CH2:18][CH2:19][CH2:20][C:21]#[CH:22])#[N:2]

Participants

4

Reactant 2

HCID 641001Pent-4-yn-1-amineHCID 178503877HCID 178503877, compound

Product 1

HCID 178446439N-Cyano-N'-{2-[(4-methyl-5-imidazolyl)methylthio]ethyl}-N"-(4-pentyn-1-yl)guanidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of N-cyano-N'-{2-[(4-methyl-5-imidazolyl)methylthio]ethyl}-S-methylisothiourea (3.00 g., 0.0111 mole) and 4-pentyn-1-amine (3.69 g., 0.0445 mole) in 60 ml. of acetonitrile was stirred at reflux for 24 hours, and then allowed to stand at room temperature for 96 hours. The solvent and excess amine were removed under reduced pressure and the residual yellow gum was purified by chromatography on 50 g. of 100-200 mesh silica gel, using gradient elution with methylene chloride/methanol (99:1-96:4). The middle fractions indicated by TLC to be pure were combined and evaporated to give 1.91 g. of yellow gum which was crystallized at -15° C from 18 ml. of ethyl acetate. The resulting white solid (1.25 g.) was recrystallized at -15° C from 10 ml. of acetonitrile to give 1.063 g. of product; m.p. 99°-103° C.

Workup

  1. temperatureat reflux for 24 hours
  2. customThe solvent and excess amine were removed under reduced pressure
  3. customthe residual yellow gum was purified by chromatography on 50 g
  4. washelution with methylene chloride/methanol (99:1-96:4)
  5. customevaporated
  6. customto give 1.91 g
  7. customof yellow gum which was crystallized at -15° C from 18 ml
  8. customThe resulting white solid (1.25 g.) was recrystallized at -15° C from 10 ml
  9. customof acetonitrile to give 1.063 g

Sources & evidence

ORD record
ord-9af05c8022dd4b2eb95c6f5dd4871e08
Source dataset
uspto-grants-1978_09
Patent number
US04112234

Reaction notes

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