Benzyloxyamine hydrochloride → HCID 64974117, compound

HRID 1752832Notes

Reaction equation

HRID 1752832 reaction equation
[Cl:1][CH:2]([CH3:6])[C:3](Cl)=[O:4].Cl.[CH2:8]([O:15][NH2:16])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CCOC(C)=O>[Cl:1][CH:2]([CH3:6])[C:3]([NH:16][O:15][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:4]

Participants

4

Reactant 2

HCID 102312Benzyloxyamine hydrochlorideHCID 1110192-Chloropropionyl chloride

Product 1

HCID 64974117HCID 64974117, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Prepared in 48% yield (0.97 g, 3.9 mmol) from the reaction of 2-chloropropanoyl chloride (1.03 g, 8.2 mmol) with O-benzylhydroxylamine, hydrochloride (1.03 g, 8.2 mmol) via general procedure A. Rf=0.43 (3:1, hexanes:EtOAc); mp=70.1-72.8° C.; 1H-NMR (500 MHz, CDCl3): δ 9.09 (br s, 1H), 7.44-7.35 (m, 5H), 4.93 (s, 4H), 4.33 (q, J=7.1 Hz, 1H), and 1.69 (d, J=6.8 Hz, 3H); 13C-NMR (126 MHz, CDCl3): δ 167.1, 134.8, 129.5, 129.1, 128.8, 78.5, 53.2, and 22.3; FT-IR: (neat): 3112 (br), 2931, 1678 (s), 1494, 1454, 1364, 1222, 1204, 1074 cm-1. HRMS ESI-MS: calculated for C10H12ClNNaO2 (M+Na)+, 236.0449; found 236.0445.

Sources & evidence

ORD record
ord-20d56d494e904c549c204bf197455116
Source dataset
uspto-grants-2015_10
Patent number
US09163033B2

Reaction notes

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