Dichloroacetyl chloride → HCID 86672884, compound

HRID 1752833Notes

Reaction equation

HRID 1752833 reaction equation
[Cl:1][CH:2]([Cl: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]([Cl: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 6593Dichloroacetyl chlorideHCID 102312Benzyloxyamine hydrochloride

Product 1

HCID 86672884HCID 86672884, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Prepared in 82% yield (2.6 g, 11.1 mmol) from the reaction of 2,2-dichloroacetyl chloride (2.0 g, 13.6 mmol) with O-benzylhydroxylamine, hydrochloride (2.15 g, 13.6 mmol) via general procedure A. Rf=0.52 (3:1, hexanes:EtOAc); 1H NMR (400 MHz, CD3CN) δ 9.89 (br s, 1H), 7.63-7.17 (m, 4H), 6.02 (s, 1H), and 4.89 (s, 2H); 13C NMR (101 MHz, CD3CN) δ 162.2, 136.1, 130.4, 129.7, 129.4, 78.8, and 65.6; IR (film) 3135 (br), 2996, 2880, 2860, 1700, 1677 (st), 1531, 1468, 1454, 1367, 1341, 1214, 1200, 1046, 1027 cm-1; HR-APPIMS calculated for C9H9Cl2NO2 (M*)+233.0005, observed 232.9976.

Sources & evidence

ORD record
ord-53f9f450fb55468896179a7e65b7f1e5
Source dataset
uspto-grants-2015_10
Patent number
US09163033B2

Reaction notes

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