2-Amino-3-methylpyridine → HCID 136187774, compound

HRID 904162Notes

Reaction equation

HRID 904162 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[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][N:14]=1>CN(C=O)C>[CH3:19][C:18]1[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])=[N:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 153472-Amino-3-methylpyridineHCID 136469822tetrahydro-1-methyl-4-oxo-1H-imidazol-2-ylidene carbamic acid

Product 1

HCID 136187774HCID 136187774, compoundYield 2.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5.0 g (21.4 mM) of the phenyl carbamate 8 and 1.2 g (10.7 mM) of 2-amino-3-methyl-pyridine in 25 ml of anhydrous DMF was heated at 55° for 3 hrs. and then cooled. The solid was collected via filtration and washed successively with cold DMF, ethyl acetate and ether. Recrystallization from ethanol and a final wash with water gave 0.07 g of the above urea as a pale yellow solid, m.p. 219°-221° C. (dec.).

Workup

  1. temperaturewas heated at 55° for 3 hrs
  2. temperatureand then cooled
  3. filtrationThe solid was collected via filtration
  4. washwashed successively with cold DMF, ethyl acetate and ether
  5. customRecrystallization from ethanol
  6. washa final wash with water

Sources & evidence

ORD record
ord-15ec5286bab149f283046416f6d008c6
Source dataset
uspto-grants-1980_10
Patent number
US04230713

Reaction notes

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