Benzyloxyamine hydrochloride → HCID 64974143, compound

HRID 1752831Notes

Reaction equation

HRID 1752831 reaction equation
[Br:1][CH:2]([CH2:6][CH3:7])[C:3](Br)=[O:4].Cl.[CH2:9]([O:16][NH2:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CCOC(C)=O>[Br:1][CH:2]([CH2:6][CH3:7])[C:3]([NH:17][O:16][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:4]

Participants

4

Reactant 2

HCID 102312Benzyloxyamine hydrochlorideHCID 1172932-Bromobutanoyl bromide

Product 1

HCID 64974143HCID 64974143, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Prepared in 72% yield (4.71 g, 17.3 mmol) from the reaction of 2-bromobutyryl bromide (5.0 g, 24 mmol) with O-benzylhydroxylamine, hydrochloride via general procedure A. Rf=0.49 (3:1, hexanes:EtOAc); mp=99.3-101.6° C.; 1H-NMR (500 MHz, CDCl3): δ 8.92 (br s, 1H), 7.52-7.31 (m, 5H), 4.93 (s, 2H), 4.12 (app q, J=7.2 Hz 1H), 2.02-1.94 (m, 2H), and 1.00 (t, J=7.0 Hz, 3H); 13C-NMR (126 MHz, CDCl3): δ 166.6, 134.8, 129.5, 129.0, 128.7, 78.4, 48.8, 28.8, and 11.8; FT-IR (neat) 3112, 2963, 2933, 2874, 1695, 1668 (s), 1528, 1496, 1454, 1364, 1177, 1089, 1023 cm-1. HRMS calculated for C11H15BrNO [M+H]+, 256.0332; found 256.0329.

Sources & evidence

ORD record
ord-75767aee936144e4b1caf72dca9de277
Source dataset
uspto-grants-2015_10
Patent number
US09163033B2

Reaction notes

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