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Ammonium Chloride → 1-methyl-1H-imidazole-2-carboxamide

HRID 1809191
Notes
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Reaction equation

HRID 1809191 reaction equation
[NH4+:1].[Cl-].C([O:5][C:6]([C:8]1[N:9]([CH3:13])[CH:10]=[CH:11][N:12]=1)=O)C>[OH-].[NH4+]>[CH3:13][N:9]1[CH:10]=[CH:11][N:12]=[C:8]1[C:6]([NH2:1])=[O:5]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 4261883ethyl 1-methyl-1H-imidazole-2-carboxylate

Product 1

HCID 4470411-methyl-1H-imidazole-2-carboxamideYield 1,969.4%

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
100 °C

Procedure

NH4Cl (0.150 g, 2.8 mmol) is added to a solution of 1-methyl-1H-imidazole-2-carboxylic acid ethyl ester (15.5 g, 101 mmol) in ammonium hydroxide 35% (112 mL) and the reaction is stirred for 6 h at 100° C. in a sealed reaction flask. The reaction is cooled to 0° C. and the solid formed filtered and washed with ice water and ether to give 1-methyl-1H-imidazole-2-carboxylic acid amide as brown crystals (6.9 g, 55%).

Workup

  1. temperatureThe reaction is cooled to 0° C.
  2. customthe solid formed
  3. filtrationfiltered
  4. washwashed with ice water and ether

Sources & evidence

ORD record
ord-1ef714ab29924cd9a926a132c9abbbd0
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08362018B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes