Hydrochloric Acid → N,N-dimethyl-1H-pyrazole-1-carboxamidine hydrochloride

HRID 1582264

Reaction equation

HRID 1582264 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.[CH3:6][N:7]([CH3:10])[C:8]#[N:9].[ClH:11]>O1CCOCC1.CCOCC>[ClH:11].[CH3:6][N:7]([CH3:10])[C:8]([N:1]1[CH:5]=[CH:4][CH:3]=[N:2]1)=[NH:9]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 1048PyrazoleHCID 15112Dimethylcyanamide

Product 1

HCID 21984986N,N-dimethyl-1H-pyrazole-1-carboxamidine hydrochlorideYield 78%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of pyrazole (1.01 g, 14.8 mmol) and dimethylcyanamide (1.20 mL, 14.8 mmol) in 1,4-dioxane (15 mL) was added HCl (4.0 N in 1,4-dioxane, 3.8 mL, 15.2 mmol) and the resultant mixture was heated to reflux for 3 hours. The reaction mixture was cooled to room temperature and diluted with dry ether (15 mL) to precipitate a yellow solid. The resultant precipitate was allowed to settle to the bottom of the flask (overnight) and the supernatant solution was decanted. The solid was dried under vacuum and provided the title compound (2.01 g, 78%). ES-MS m/z 139 (M+H).

Workup

  1. temperatureto reflux for 3 hours
  2. customto precipitate a yellow solid
  3. custombottom of the flask (overnight)
  4. customthe supernatant solution was decanted
  5. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-fc4be28039784466ad3ba07421cfb60b
Source dataset
uspto-grants-2004_05
Patent number
US06734191B2

Linked notes

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