2-Propoxybenzamide → Ethyl 2-n-propoxybenzimidate fluoroborate

HRID 437417

Reaction equation

HRID 437417 reaction equation
[F:1][B-:2]([F:5])([F:4])[F:3].[CH2:6]([O+](CC)CC)[CH3:7].[CH2:13]([O:16][C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19]([NH2:21])=[O:20])[CH2:14][CH3:15]>C(Cl)Cl>[F:1][B-:2]([F:5])([F:4])[F:3].[CH2:13]([O:16][C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19](=[NH:21])[O:20][CH2:6][CH3:7])[CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 430512-PropoxybenzamideHCID 2723982Triethyloxonium tetrafluoroborate

Product 1

HCID 86734866Ethyl 2-n-propoxybenzimidate fluoroborateYield 85.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of triethyloxonium fluoroborate (33.0 g., 0.175 mole) in methylene chloride (75 ml.) was added during 10 minutes to a stirred solution of 2-n-propoxybenzamide (31.3 g., 0.175 mole) in methylene chloride (150 ml.). The solution was stirred for an additional 18 hours at room temperature. The solution was concentrated to about one-fifth volume and was diluted with diethyl ether to precipitate the ethyl 2-n-propoxybenzimidate fluoroborate (44.0 g., 85% yield), m.p. 108°-112°.

Workup

  1. concentrationThe solution was concentrated to about one-fifth volume
  2. additionwas diluted with diethyl ether

Sources & evidence

ORD record
ord-90a9e484b4b9448dba72f113b0cb04ec
Source dataset
uspto-grants-1977_06
Patent number
US04031093

Linked notes

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