Ethylamine hydrochloride → Benzamide, 3,4-difluoro-N-ethyl-

HRID 44331

Reaction equation

Cl.[CH2:2]([NH2:4])[CH3:3].[F:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[F:15])[C:9]([OH:11])=O>>[F:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[F:15])[C:9]([NH:4][CH2:2][CH3:3])=[O:11]

Participants

Reactant 2

HCID 11198Ethylamine hydrochloride

HCID 991663,4-Difluorobenzoic acid

Product 1

HCID 17683011Benzamide, 3,4-difluoro-N-ethyl-Yield 56%

Procedure

Using ethylamine hydrochloride and 3,4-difluorobenzoic acid in the general procedure for coupling of amines to carboxylic acids (Scheme C), the title compound was obtained (56% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.12 (t, J=7.20 Hz, 3 H) 3.28 (qd, J=7.24, 5.56 Hz, 2 H) 7.55 (dt, J=10.48, 8.40 Hz, 1 H) 7.73 (m, J=7.33, 4.74, 2.08, 1.14, 1.14 Hz, 1 H) 7.88 (ddd, J=11.75, 7.83, 2.15 Hz, 1 H) 8.58 (t, J=4.93 Hz, 1 H). ESI-MS: m/z 186.1 (M+H)+. mp=94.1-96.2° C.

Sources & evidence

ORD record: ord-af4ed04957e94568a015c60862111292
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541417B2

Linked notes

Loading…