Water → HCID 178507501, compound

HRID 1608829Notes

Reaction equation

HRID 1608829 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6]C(=O)[O:4][C:2]2=O.[NH2:13][CH2:14][CH2:15][C:16]1[CH:20]=[CH:19][NH:18][N:17]=1.O>O1CCOCC1.C(OCC)(=O)C>[NH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=1[C:2]([NH:13][CH2:14][CH2:15][C:16]1[CH:20]=[CH:19][NH:18][N:17]=1)=[O:4]

Participants

6

Reactant 3

HCID 962WaterHCID 8359Isatoic AnhydrideHCID 178510849HCID 178510849, compound

Product 1

HCID 178507501HCID 178507501, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A slurry containing 17.7 g (O.109 mol) of isatoic anhydride in 80 ml of dioxane was slowly added to a cold (0° C.) solution of 12.1 g (O.109 mol) of 3-(2-aminoethyl)pyrazole in 150 ml of dioxane, under nitrogen. The reaction solution was gradually warmed to room temperature and allowed to react overnight. When the reaction was complete, as indicated by thin layer chromatography, water was added and the solution was reduced to dryness under reduced pressure. The resultant residue was dissolved in an ethyl acetate/aqueous sodium bicarbonate mixture. The resulting layers were separated and the organic layer was washed with water and reduced to dryness to provide an oil. This oil was purified by crystallization from dichloromethane, followed by recrystallization from an ethyl acetate/diethyl ether solution, to provide 12.8 g of the desired subtitled intermediate (m.p. 97°-99° C.).

Workup

  1. additionA slurry containing 17.7 g (O
  2. customto react overnight
  3. additionwas added
  4. customThe resulting layers were separated
  5. washthe organic layer was washed with water
  6. customto provide an oil
  7. customThis oil was purified by crystallization from dichloromethane
  8. customfollowed by recrystallization from an ethyl acetate/diethyl ether solution

Sources & evidence

ORD record
ord-f1ed746cd1214d299463762eeafffc57
Source dataset
uspto-grants-1995_03
Patent number
US05397798

Reaction notes

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