o-Anisamide, 3-methyl- → HCID 21504428, compound

HRID 1288272Notes

Reaction equation

HRID 1288272 reaction equation
[B-](F)(F)(F)F.[CH3:6][CH2:7][O+](CC)CC.[CH3:13][O:14][C:15]1[C:23]([CH3:24])=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([NH2:19])=[O:18]>C(Cl)Cl>[CH3:13][O:14][C:15]1[C:23]([CH3:24])=[CH:22][CH:21]=[CH:20][C:16]=1[C:17](=[NH:19])[O:18][CH2:6][CH3:7]

Participants

4

Reactant 2

HCID 56081o-Anisamide, 3-methyl-HCID 2723982Triethyloxonium tetrafluoroborate

Product 1

HCID 21504428HCID 21504428, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of triethyloxonium borofluoride (23 g.) in anhydrous methylene chloride (60 ml.) was added to a solution of 2-methoxy-3-methylbenzamide [19.7 g; prepared as described in French Patent M.21] in anhydrous methylene chloride (200 ml.). The mixture was kept at room temperature for 3 days, concentrated to about 120 ml. and diluted with anhydrous diethyl ether (300 ml.). The solid which separated was filtered off and washed with anhydrous diethyl ether to give ethyl 2-methoxy-3-methylbenzimidate borofluoride (28.7 g.), m.p. 93°-96° C., which was pure enough for use in the next stage of the synthesis. An aliquot was recrystallised from a mixture of anhydrous methylene chloride and anhydrous diethyl ether to give pure ethyl 2-methoxy-3-methylbenzimidate borofluoride, m.p. 102°-104° C.

Workup

  1. concentrationconcentrated to about 120 ml
  2. additionand diluted with anhydrous diethyl ether (300 ml.)
  3. customThe solid which separated
  4. filtrationwas filtered off
  5. washwashed with anhydrous diethyl ether

Sources & evidence

ORD record
ord-cb29314ad3c640bda496207d73672de7
Source dataset
uspto-grants-1976_10
Patent number
US03987160

Reaction notes

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