Triethyloxonium tetrafluoroborate → Ethyl 2-cyclopropylmethoxybenzimidate fluoroborate

HRID 2082719Notes

Reaction equation

HRID 2082719 reaction equation
[F:1][B-:2]([F:5])([F:4])[F:3].[CH2:6]([O+](CC)CC)[CH3:7].[CH:13]1([CH2:16][O:17][C:18]2[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=2[C:20]([NH2:22])=[O:21])[CH2:15][CH2:14]1>C(Cl)Cl>[F:1][B-:2]([F:5])([F:4])[F:3].[CH:13]1([CH2:16][O:17][C:18]2[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=2[C:20](=[NH:22])[O:21][CH2:6][CH3:7])[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 2723982Triethyloxonium tetrafluoroborateHCID 27280292-(Cyclopropylmethoxy)benzamide

Product 1

HCID 86734870Ethyl 2-cyclopropylmethoxybenzimidate fluoroborateYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of triethyloxonium fluoroborate (99.1 g., 0.522 mole) in methylene chloride (225 ml.) was added to a stirred solution of 2-cyclopropylmethoxybenzamide (99.2 g., 0.518 mole) in methylene chloride (450 ml.). The mixture was stirred at 22° for 18 hours. The solution was concentrated to about one-fifth volume and then diluted with diethyl ether. The precipitated solid was recrystallized from methylene chloride - diethyl ether to give ethyl 2-cyclopropylmethoxybenzimidate fluoroborate (104.7 g., 65.7%), m.p. 120°-121°. To a stirred, cooled (ice-water) mixture of the fluoroborate (104.7 g.) in ethanol (100 ml.) was added 400 ml. of 6% ethanolic ammonia. The mixture was stirred for 18 hours at 20°. The mixture was concentrated and the residue partitioned between diethyl ether and 3N sodium hydroxide. The ether layer was washed with brine and dried over sodium sulfate. The dried solution was treated with hydrogen chloride. The precipitate was recrystallized from methylene chloride-diethyl ether to give 2-cyclopropylmethoxybenzamidine hydrochloride (71.5 g., 92.5% from fluoroborate), m.p. 166°-171°.

Workup

  1. concentrationThe solution was concentrated to about one-fifth volume
  2. additiondiluted with diethyl ether
  3. customThe precipitated solid was recrystallized from methylene chloride - diethyl ether

Sources & evidence

ORD record
ord-a049b5b98e884c6cb416e418f0ac24a5
Source dataset
uspto-grants-1978_04
Patent number
US04082751

Reaction notes

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