Hydrochloric Acid → 2,3-Dimethoxy-benzamidine

HRID 264754Notes

Reaction equation

HRID 264754 reaction equation
C[Si](C)(C)[NH:3][Si](C)(C)C.C([Li])CCC.[CH3:15][O:16][C:17]1[C:24]([O:25][CH3:26])=[CH:23][CH:22]=[CH:21][C:18]=1[C:19]#[N:20].Cl>CCOCC.CCCCCC>[CH3:15][O:16][C:17]1[C:24]([O:25][CH3:26])=[CH:23][CH:22]=[CH:21][C:18]=1[C:19]([NH2:3])=[NH:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 13838HexamethyldisilazaneHCID 218622,3-DimethoxybenzonitrileHCID 178418339Butyllithium

Product 1

HCID 37009942,3-Dimethoxy-benzamidine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

To a solution of 20 g 1,1,1,3,3,3-hexamethyldisilazane in 150 ml dry ether was added 5 mL 2.4M n-butyllithium in hexane. After 10 min at room temperature, 16.3 g 2,3-dimethoxybenzonitrile was added in one portion and the mixture was kept at room temperature for 16 h. The reaction mixture was then poured onto excess 3N HCl. The aqueous layer was separated, basified with 50% NaOH and the product was extracted three times with 10% methanol in methylene chloride. The combined organic extracts were dried over potassium carbonate and the solvents removed in vacuo to afford 2,3-dimethoxybenzamidine as a glassy solid.

Workup

  1. waitthe mixture was kept at room temperature for 16 h
  2. customThe aqueous layer was separated
  3. extractionthe product was extracted three times with 10% methanol in methylene chloride
  4. dry with materialThe combined organic extracts were dried over potassium carbonate
  5. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-d77aed33f0414035a9d400eea285924e
Source dataset
uspto-grants-1997_07
Patent number
US05646281

Reaction notes

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