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

HRID 8926

Reaction equation

HRID 8926 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-f311fc80c113400083d5a3966db9b7c5
Source dataset
uspto-grants-2006_08
Patent number
US07091217B2

Linked notes

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