Ethylenediamine → HCID 24752186, compound

HRID 553411Notes

Reaction equation

[CH2:1]([NH2:4])[CH2:2][NH2:3].[F:5][C:6]([F:18])([F:17])[O:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11](Cl)=O.[C:19](#[N:21])C>>[F:5][C:6]([F:18])([F:17])[O:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[CH2:11][N:3]1[CH2:2][CH2:1][N:4]([CH2:11][C:10]2[CH:14]=[CH:15][CH:16]=[C:8]([O:7][C:6]([F:5])([F:17])[F:18])[CH:9]=2)[C:19]1=[NH:21]

Participants

Reactant 3

HCID 3301Ethylenediamine

HCID 6342Acetonitrile

HCID 5228543-(Trifluoromethoxy)benzoyl chloride

Product 1

HCID 24752186HCID 24752186, compound

Procedure

The title compound was prepared in three steps as described in Procedure D. In the first step, ethylenediamine was reacted in acetonitrile with 3-(trifluoromethoxy)benzoylchloride (2 eq) in the presence of TEA to give the N,N′-dibenzoylated ethylenediamine upon aqueous work-up. After the last step (reaction with cyanogen bromide), the crude product was isolated upon aqueous work-up, recrystallized from diethyl ether and the title compound isolated as the hydrogen bromide salt. MS (ES+) m/z 434 ([M+1]+, 100); HR-MS: 434.1299 ([M+1]+, C19H18F6N3O2; calc. 434.13032).

Sources & evidence

ORD record: ord-8fa588fb4cd9476d9bdde23f151608de
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048877B2

Reaction notes

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