Dimethyl N-cyanodithioiminocarbonate → HCID 20303949, compound

HRID 1732571Notes

Reaction equation

HRID 1732571 reaction equation
[NH2:1][CH2:2][CH2:3][S:4][CH2:5][C:6]1[O:7][C:8]2[CH:14]=[C:13]([CH2:15][N:16]([CH3:18])[CH3:17])[CH:12]=[CH:11][C:9]=2[CH:10]=1.[C:19]([N:21]=[C:22](SC)[S:23][CH3:24])#[N:20]>C(#N)C>[C:19]([NH:21][C:22](=[N:1][CH2:2][CH2:3][S:4][CH2:5][C:6]1[O:7][C:8]2[CH:14]=[C:13]([CH2:15][N:16]([CH3:18])[CH3:17])[CH:12]=[CH:11][C:9]=2[CH:10]=1)[S:23][CH3:24])#[N:20]

Participants

4

Reactant 2

HCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 203039642-(2-Aminoethylthiomethyl)-6-(dimethylaminomethyl)benzofuran

Product 1

HCID 20303949HCID 20303949, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-(2-aminoethylthiomethyl)-6-(dimethylaminomethyl)benzofuran (12.0 g, 0.0454 mole) and dimethyl cyanodithioimidocarbonate (7.0 g., 0.048 mole) in acetonitrile (48 ml.) is allowed to stand 2 hours at room temperature. The solvent is evaporated at reduced pressure and the viscous oily residue is chromatographed on a column of 250 g. of silica gel. Elution with 8% methanol in chloroform removes the product. There is obtained 14.6 g. (89%) of N-cyano-N'-[2-(6-dimethylaminomethyl-2-(benzofuranylmethylthio)ethyl]-S-methylisothiourea as a yellow oil which gradually crystallizes, m.p. 98°-100° C.

Workup

  1. customThe solvent is evaporated at reduced pressure
  2. customthe viscous oily residue is chromatographed on a column of 250 g
  3. washElution with 8% methanol in chloroform
  4. customremoves the product
  5. customThere is obtained 14.6 g
  6. custom(89%) of N-cyano-N'-[2-(6-dimethylaminomethyl-2-(benzofuranylmethylthio)ethyl]-S-methylisothiourea as a yellow oil which gradually crystallizes

Sources & evidence

ORD record
ord-b11b07b9a3a34b868ccc4f6c41942912
Source dataset
uspto-grants-1980_12
Patent number
US04238487

Reaction notes

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