Ethyl isocyanate → HCID 11849858, compound

HRID 1717241Notes

Reaction equation

HRID 1717241 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH2:13][CH2:14][CH3:15])=[C:11]([C:16]([NH:18][CH:19]3[CH2:21][CH2:20]3)=[O:17])[N:10]=[N:9]2)=[CH:4][CH:3]=1.[CH2:22]([N:24]=[C:25]=[O:26])[CH3:23]>CN(C1C=CN=CC=1)C.ClCCl>[CH:19]1([NH:18][C:16]([C:11]2[N:10]=[N:9][N:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:25]([NH:24][CH2:22][CH3:23])=[O:26])=[CH:3][CH:4]=3)[C:12]=2[CH2:13][CH2:14][CH3:15])=[O:17])[CH2:20][CH2:21]1

Participants

5

Reactant 2

HCID 8022Ethyl isocyanateHCID 685175481-(4-aminophenyl)-N-cyclopropyl-5-propyl-1H-1,2,3-triazole-4-carboxamide

Product 1

HCID 11849858HCID 11849858, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(4-aminophenyl)-N-cyclopropyl-5-propyl-1H-1,2,3-triazole-4-carboxamide (0.40 g) obtained in Example 1d) and DMAP (0.34 g) in dichloromethane (14 ml) was added ethyl isocyanate (0.79 ml) at room temperature and the mixture was stirred for 3 hr. The reaction mixture was diluted with dichloromethane, and washed with saturated aqueous sodium hydrogen carbonate solution. The organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column (ethyl acetate/hexane=1/1 to ethyl acetate), and the obtained product was recrystallized from ethyl acetate-diethyl ether to give the title compound as a white powder (0.12 g, 49%).

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column (ethyl acetate/hexane=1/1 to ethyl acetate)
  5. customthe obtained product was recrystallized from ethyl acetate-diethyl ether

Sources & evidence

ORD record
ord-0405927385c74c299ece06b2c4ada3d1
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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