2-Methoxyacetohydrazide → 9-Chloro-2-methoxymethyl-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one

HRID 1786170

Reaction equation

C([O:3][C:4](=O)[NH:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[C:13]#[N:14])C.[CH3:16][O:17][CH2:18][C:19]([NH:21][NH2:22])=O>>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]2[NH:5][C:4](=[O:3])[N:22]3[N:21]=[C:19]([CH2:18][O:17][CH3:16])[N:14]=[C:13]3[C:7]=2[CH:8]=1

Participants

Reactant 2

HCID 27595322-Methoxyacetohydrazide

HCID 21779762Ethyl 4-chloro-2-cyanophenylcarbamate

Product 1

HCID 1363478699-Chloro-2-methoxymethyl-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-oneYield 88%

Procedure

As described for example 1a) (4-chloro-2-cyano-phenyl)-carbamic acid ethyl ester (71.0 g, 316 mmol) using methoxymethyl-carboxylic acid hydrazide instead of cyclopropane-carboxylic acid hydrazide, was converted to the title compound (73.9 g, 88%) which was obtained as a yellow solid. MS: m/e=264.9 [M+H]+.

Sources & evidence

ORD record: ord-966f88043c0a4b97b0f02e8322057c1f
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07507729B2

Linked notes

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