Ammonium Chloride → Methyl 2-(3-carbamimidoyl-1H-1,2,4-triazol-1-yl)acetate hydrochloride

Reaction equation

[C:1]([C:3]1[N:7]=[CH:6][N:5]([CH2:8][C:9]([O:11][CH2:12]C)=[O:10])[N:4]=1)#[N:2].C[O-].[Na+].[Cl-:17].[NH4+:18]>>[ClH:17].[C:1]([C:3]1[N:7]=[CH:6][N:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[N:4]=1)(=[NH:2])[NH2:18]

Participants

Reactant 3

HCID 25517Ammonium Chloride

HCID 10942334Sodium Methoxide

HCID 60710264ethyl 2-(3-cyano-1H-1,2,4-triazol-1-yl)acetate

Product 1

HCID 90042811Methyl 2-(3-carbamimidoyl-1H-1,2,4-triazol-1-yl)acetate hydrochlorideYield 55%

Procedure

Ethyl 2-(3-cyano-1H-1,2,4-triazol-1-yl)acetate (2 g, 11.2 mmol) was reacted with sodium methoxide (0.85 g, 15.68 mmol) and ammonium chloride (0.89 g, 16.8 mmol) according to the procedure as described in Example 61, Step B to give the title compound as a white solid (1.35 g, 55%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record: ord-002c5003137c447c984d7d10eac4f92b
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340538B2

Reaction notes

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