Ethylamine → 2-(4-Bromo-phenyl)-N-ethyl-isobutyramide

HRID 1453029Notes

Reaction equation

HRID 1453029 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH3:12])[C:9]([OH:11])=O)=[CH:4][CH:3]=1.C(OCC)(=O)CC(O)=O.[CH2:23]([NH2:25])[CH3:24].BrC1C=CC([C@H](N)C)=CC=1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:13])([CH3:12])[C:9]([NH:25][CH2:23][CH3:24])=[O:11])=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 6341EthylamineHCID 70615Monoethyl malonateHCID 853000(R)-4-bromo-alpha-methylbenzylamineHCID 109336792-(4-Bromophenyl)-2-methylpropanoic acid

Product 1

HCID 587627102-(4-Bromo-phenyl)-N-ethyl-isobutyramideYield 82%

Procedure

The title compound was prepared as described in Step 1 of Example A(39), where 2-(4-bromophenyl)-2-methyl propionic acid was substituted for ethyl hydrogen malonate and ethyl amine was substituted for (R)-(+)-1-(4-bromophenyl)ethylamine on that example. Yield 82%. 1H NMR (CDCl3) δ: 1.01 (t, J=5.3 Hz, 3H), 1.55 (s, 6H),), 3.2 (q, J=7.0, 5.3, 2H), 5.15 (brs, 1H), 7.22-7.26 (m, 2H), 7.46-7.50 (m, 2H).

Sources & evidence

ORD record
ord-e295cda42c5a4deab0a51c0e9db41c96
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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