Propargylamine → 1-cyano-3-[2-[[6-[(dimethylamino)methyl]-1-benzofuran-2-yl]methylsulfanyl]ethyl]-2-prop-2-ynylguanidine

HRID 1732581Notes

Reaction equation

HRID 1732581 reaction equation
[C:1]([NH:3][C:4](=[N:7][CH2:8][CH2:9][S:10][CH2:11][C:12]1[O:13][C:14]2[CH:20]=[C:19]([CH2:21][N:22]([CH3:24])[CH3:23])[CH:18]=[CH:17][C:15]=2[CH:16]=1)SC)#[N:2].[CH2:25]([NH2:28])[C:26]#[CH:27]>C(#N)C>[C:1]([NH:3][C:4]([NH:7][CH2:8][CH2:9][S:10][CH2:11][C:12]1[O:13][C:14]2[CH:20]=[C:19]([CH2:21][N:22]([CH3:24])[CH3:23])[CH:18]=[CH:17][C:15]=2[CH:16]=1)=[N:28][CH2:25][C:26]#[CH:27])#[N:2]

Participants

4

Reactant 2

HCID 239041PropargylamineHCID 20303949HCID 20303949, compound

Product 1

HCID 1784575591-cyano-3-[2-[[6-[(dimethylamino)methyl]-1-benzofuran-2-yl]methylsulfanyl]ethyl]-2-prop-2-ynylguanidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solutiion of N-cyano-N'-[2-(6-dimethylaminomethyl)-2-benzofuranylmethylthio)ethyl]-S-methylisothiourea (Example 1, Step F) (6.55 g., 0.018 mole) and propargylamine (4.0 g., 0.073 mole) in acetonitrile (100 ml.) is heated in a sealed pressure vessel at 110°-120° C. for 36 hours. The reaction solution is then evaporated at reduced pressure. N-cyano-N'-[2-(6-dimethylaminomethyl-2-benzofuranylmethylthio)ethyl]-N"-(2-propynyl)guanidine is obtained when the residual oil is chromatographed on silica gel with elution by an 8% solution of methanol in chloroform.

Workup

  1. customThe reaction solution is then evaporated at reduced pressure

Sources & evidence

ORD record
ord-c8ba4bcfaece473085f21629448f7c19
Source dataset
uspto-grants-1980_12
Patent number
US04238487

Reaction notes

Loading…