Benzylamine → N-Benzyl-2-bromo-2-methylpropanamide

HRID 1752829Notes

Reaction equation

HRID 1752829 reaction equation
[Br:1][C:2]([CH3:7])([CH3:6])[C:3](Br)=[O:4].[CH2:8]([NH2:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CCOC(C)=O>[Br:1][C:2]([CH3:7])([CH3:6])[C:3]([NH:15][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:4]

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 886852-Bromo-2-methylpropionyl bromide

Product 1

HCID 151608N-Benzyl-2-bromo-2-methylpropanamideYield 91%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Prepared in 91% yield (10.7 g, 42 mmol) from the reaction of 2-bromo-2-methylpropanoyl bromide (10.6 g, 46 mmol) with benzylamine (5.1 mL, 46 mmol) via general procedure A. Rf=0.84 (3:1, hexanes:EtOAc); mp 73.4-75.5° C.; 1H NMR (400 MHz, CDCl3): δ 7.41-7.23 (m, 1H), 7.03 (br s, 1H), 4.46 (d, J=5.8 Hz, 1H), and 1.99 (s, 1H); 13C NMR (125 MHz, CDCl3): δ 172.0, 137.8, 128.8, 127.6, 127.6, 62.8, 44.4, and 32.6; IR (neat) 3291 (br), 3065, 301, 3008, 2938, 2919, 1642 (s), 1533 cm-1; HRMS (ESI) calculated 256.0332 C11H15BrNO [M+H]+, observed 256.0329.

Sources & evidence

ORD record
ord-54acef46f0df48898de318253c14b509
Source dataset
uspto-grants-2015_10
Patent number
US09163033B2

Reaction notes

Loading…