Hydrochloric Acid → 2,3-Dimethoxy-benzamidine

HRID 1490232Notes

Reaction equation

HRID 1490232 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 1,1,1,3,3,3-hexamethyldisilazane (20 g) in dry ether (150 mL) was added 2.4M n-butyllithium in hexane (5 mL). After 10 min at room temperature, 2,3-Dimethoxybenzonitrile (16.3 g) was added in one portion and the mixture was kept at room temperature for 16 h. The reaction mixture was the poured onto excess 3N HCl. The aqueous layer was separated, basified with 50% NaOH and the product was exuacted three times with 10% methanol in methylene chloride. The combined organic extracts were dried over magnesium sulfate and the solvents removed in vacuo to afford 2,3-Dimethoxy-benzamidine as a glassy solid.

Workup

  1. waitthe mixture was kept at room temperature for 16 h
  2. customThe aqueous layer was separated
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-577a95431e0744bfb9f0edf6fb489017
Source dataset
uspto-grants-1997_10
Patent number
US05681956

Reaction notes

Loading…