Oxalyl chloride → 2-Azido-n-(chloromethyl)-acetamide

HRID 1018446Notes

Reaction equation

[N:1]([CH2:4][C:5]([NH:7][CH2:8]O)=[O:6])=[N+:2]=[N-:3].C(Cl)(=O)C([Cl:13])=O>>[N:1]([CH2:4][C:5]([NH:7][CH2:8][Cl:13])=[O:6])=[N+:2]=[N-:3]

Participants

Reactant 2

HCID 65578Oxalyl chloride

HCID 184014742-azido-N-(hydroxymethyl)-acetamide

Product 1

HCID 184014732-Azido-n-(chloromethyl)-acetamideYield 75%

Procedure

To 2-azido-N-(hydroxymethyl)-acetamide (650 mg, 5 mmol) at −10° C. oxalyl chloride (635 mg, 5 mmol) was added. After 10 min gas evolution had ceased. The mixture was diluted in CDCl3. NMR-Spectrum in CDCl3: 4.1 (s, 2H), 5.2 (d, 2H, J=10 Hz), 7.3 (broad signal, 1H) ppm. The NMR was consitent with 2-azido-N-(chloromethyl)-acetamide (yield 75%).

Workup

additionThe mixture was diluted in CDCl3

Sources & evidence

ORD record: ord-b7a587134486417f84f5d7428eab1753
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06482818B2

Reaction notes

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