2-Amino-5-chloropyridine → 1-(5-Chloro-2-pyridinyl)-3-(tetrahydro-1-methyl-4-oxo-1H-imidazol-2-ylidene) urea

HRID 904159Notes

Reaction equation

HRID 904159 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]=[CH:17][C:16]([Cl:19])=[CH:15][N:14]=1>CN(C=O)C>[Cl:19][C:16]1[CH:17]=[CH:18][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]=1

Participants

4

Reactant 2

HCID 661742-Amino-5-chloropyridineHCID 136469822tetrahydro-1-methyl-4-oxo-1H-imidazol-2-ylidene carbamic acid

Product 1

HCID 1360068601-(5-Chloro-2-pyridinyl)-3-(tetrahydro-1-methyl-4-oxo-1H-imidazol-2-ylidene) urea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.3 g. (10 mM) of the phenyl carbamate 8 and 3.0 g. (23 mM) of 2-amino-5-chloropyridine in 25 ml of anhydrous DMF was heated at 45°-50° C. for 2 hrs., cooled and filtered. The collected solid was washed successively with cold DMF, ethyl acetate, and ether to give 1.6 g of the above urea as a yellow solid, m.p. 250°-251° C. (dec.).

Workup

  1. additionA mixture of 2.3 g
  2. temperature, cooled
  3. filtrationfiltered
  4. washThe collected solid was washed successively with cold DMF, ethyl acetate, and ether

Sources & evidence

ORD record
ord-1efdd196ce4241d3a5978139f4016e77
Source dataset
uspto-grants-1980_10
Patent number
US04230713

Reaction notes

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