Triethylamine → Naphthalene-1-carboxylic acid 1-(4-bromo-phenyl)-1-ethoxy-methylideneamide

HRID 516495Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[NH:10])[O-:9])=[CH:4][CH:3]=1.[CH2:11](N(CC)CC)[CH3:12].[C:18]1([C:28](Cl)=[O:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:10][C:28]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=2)=[O:29])[O:9][CH2:11][CH3:12])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 10 °C

Procedure

4-Bromobenzene carboximidate (6.0 g, 0.0263 mol) and triethyl amine (3.0 g, 0.0297 mol) is dissolved in toluene (15 ml). It is then cooled to 10° C. 1-naphthoyl chloride (5.0 g, 0.0263 mol) in toluene (10 ml) is added slowly to the reaction mixture over a period of 15 minutes under a nitrogen atmosphere. The reaction mixture is then stirred for 10 hours at 25° C. It is then filtered to remove the triethyl amine hydrochloride salt and the filtrate is concentrated to obtain a yellowish solid, which is washed with hexane (20 ml) and methanol (10 ml) respectively to obtain the pure desired product (Yield=7.5 g (75%)).

Workup

filtrationIt is then filtered
customto remove the triethyl amine hydrochloride salt
concentrationthe filtrate is concentrated
customto obtain a yellowish solid, which
washis washed with hexane (20 ml) and methanol (10 ml) respectively

Sources & evidence

ORD record: ord-6285171a1c0244e6a7e3b2a406fc6d44
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09113536B2

Reaction notes

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