Hydrochloric Acid → 1-Methyl-1H-imidazole-2-carbohydrazide

HRID 1889000Notes

Reaction equation

HRID 1889000 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:7]([NH:9][NH:10]C(OC(C)(C)C)=O)=[O:8].Cl>O1CCOCC1>[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:7]([NH:9][NH2:10])=[O:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66598991HCID 66598991, compound

Product 1

HCID 173802931-Methyl-1H-imidazole-2-carbohydrazide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of t-butyl 2-[(1-methyl-1H-imidazol-2-yl)carbonyl]hydrazinecarboxylate (I45) (143 mg, 0.595 mmol) in 1,4-dioxane (1.5 ml) stirred under argon at room temp was added a solution of hydrochloric acid (4 M) in dioxane (2.232 ml, 8.93 mmol). The reaction mixture was stirred at RT for 48 hr, then evaporated in vacuo and the residue added to an SCX column and eluted with dichloromethane (100 ml) followed by 5% MeOH/DCM (50 ml), 10% MeOH/DCM (30 ml), and 2M NH3/MeOH (50 ml) to afford the required product as a chartreuse solid in 73.1 mg, which was used without further purification in the next step.

Workup

  1. customevaporated in vacuo
  2. additionthe residue added to an SCX column
  3. washeluted with dichloromethane (100 ml)

Sources & evidence

ORD record
ord-931343ce0db44dd6a0acce7f2878aa43
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Reaction notes

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