Triethyloxonium tetrafluoroborate → Ethyl 4-methyl-2-propoxybenzimidate tetrafluoroborate

HRID 1460979Notes

Reaction equation

[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[C:4]([O:11][CH2:12][CH2:13][CH3:14])[CH:3]=1.[F:15][B-:16]([F:19])([F:18])[F:17].[CH2:20]([O+](CC)CC)[CH3:21]>>[F:15][B-:16]([F:19])([F:18])[F:17].[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](=[NH:8])[O:7][CH2:20][CH3:21])=[C:4]([O:11][CH2:12][CH2:13][CH3:14])[CH:3]=1

Participants

Reactant 2

HCID 2723982Triethyloxonium tetrafluoroborate

HCID 212507564-Methyl-2-propoxybenzamide

Product 1

HCID 21250823Ethyl 4-methyl-2-propoxybenzimidate tetrafluoroborate

Procedure

reaction of 4-methyl-2-propoxybenzamide (I196 g) with triethyloxonium tetrafluoroborate yielded crude ethyl 4-methyl-2-propoxybenzimidate tetrafluoroborate which on reaction with a saturated solution of ethanolic ammonia and treatment with hydrochloric acid yielded 4-methyl-2-propoxybenzamidine hydrochloride, (8.74 g), m.p. 228°-30° C.;

Sources & evidence

ORD record: ord-91ff3910d7b741aeb5668e597bbef485
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05073559

Reaction notes

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