Methylamine → N-cyano-N'-[2-(6-dimethylaminomethyl-2-benzofuranylmethylthio)ethyl]-N"-methylguanidine

HRID 1732572Notes

Reaction equation

HRID 1732572 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].[CH3:25][NH2:26]>C(O)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:26][CH3:25])#[N:2]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 20303949HCID 20303949, compound

Product 1

HCID 54406222N-cyano-N'-[2-(6-dimethylaminomethyl-2-benzofuranylmethylthio)ethyl]-N"-methylguanidineYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-cyano-N'-[2-(6-dimethylaminomethyl-2-benzofuranylmethylthio)ethyl]-S-methylisothiourea (8.8 g., 0.024 mole) and methylamine (31 g.) in ethanol (90 ml.) is allowed to stand at room temperature for 3 hours. The solvent is evaporated at reduced pressure. The residual oil gradually crystallizes, m.p. 62°-65° C. Two crystallizations of this product from acetonitrile-ether gives 7.0 g, (84%) of N-cyano-N'-[2-(6-dimethylaminomethyl-2-benzofuranylmethylthio)ethyl]-N"-methylguanidine as white needles, m.p. 115.5°-117.5° C.

Workup

  1. customThe solvent is evaporated at reduced pressure
  2. customThe residual oil gradually crystallizes
  3. customTwo crystallizations of this product from acetonitrile-ether

Sources & evidence

ORD record
ord-2f3ca2f009f14083b44a16cd0d3e19b4
Source dataset
uspto-grants-1980_12
Patent number
US04238487

Reaction notes

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