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2-Amino-4-methylpyridine → 1-(4-Methyl-2-pyridinyl)-3-(tetrahydro-1-methyl-4-oxo-1H-imidazol-2-ylidene) urea

HRID 904154
Notes
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Reaction equation

HRID 904154 reaction equation
[CH3:1][N:2]1[CH2:6][C:5](=[O:7])[NH:4][C:3]1=[N:8][C:9](=[O:11])O.[NH2:12][C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][N:14]=1>CN(C=O)C>[CH3:19][C:17]1[CH:16]=[CH:15][N:14]=[C:13]([NH:12][C:9]([N:8]=[C:3]2[NH:4][C:5](=[O:7])[CH2:6][N:2]2[CH3:1])=[O:11])[CH:18]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 15332-Amino-4-methylpyridineHCID 136469822tetrahydro-1-methyl-4-oxo-1H-imidazol-2-ylidene carbamic acid

Product 1

HCID 1361496961-(4-Methyl-2-pyridinyl)-3-(tetrahydro-1-methyl-4-oxo-1H-imidazol-2-ylidene) ureaYield 12.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 3.0 g (12.8 mM) of the phenyl carbamate 8 and 2.8 g (25.7 mM) of 2-amino-4-methylpyridine in 25 ml of anhydrous DMF was stirred at 25° C. for 5 hrs., filtered and the filtrate diluted with 150 ml of water. The resulting precipitate was collected and recrystallized from ethanol to give 0.6 g of the above urea as a pale yellow solid, m.p. 231°-232° C. (dec.).

Workup

  1. filtration, filtered
  2. additionthe filtrate diluted with 150 ml of water
  3. customThe resulting precipitate was collected
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-75b3931a461745ab84bad3a2f9495499
Source dataset
uspto-grants-1980_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04230713

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes