Toluene → HCID 178469938, compound

HRID 1157943Notes

Reaction equation

HRID 1157943 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:10][C:11]([C:13]1[C:14]([NH:18][NH:19]C(OC(C)(C)C)=O)=[N:15][NH:16][CH:17]=1)=[O:12])[CH3:9].C1(C)C=CC=CC=1.[Cl:34]CCl>>[ClH:34].[ClH:34].[CH2:8]([O:10][C:11]([C:13]1[C:14]([NH:18][NH2:19])=[N:15][NH:16][CH:17]=1)=[O:12])[CH3:9]

Participants

5

Reactant 4

HCID 1140TolueneHCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 178469939HCID 178469939, compound

Product 1

HCID 178469938HCID 178469938, compound

Procedure

After adding 25 ml of trifluoroacetic acid to a 50 ml solution of 3.30 g of 3-(N′-t-butoxycarbonylhydrazino)-1H-pyrazole-4-carboxylic acid ethyl ester in dichloromethane, the mixture was stirred for 2 hours at room temperature. Next, 100 ml of toluene was added and the solvent was removed under reduced pressure. The residue was dissolved in a small amount of methanol, and after adding a 4N hydrogen chloride-ethyl acetate solution until the solution reached acidity, the solvent was removed under reduced pressure. The residue was treated with 50 ml of t-butyl methyl ether, and the solid was collected by filtration and dried under reduced pressure to obtain the target compound (3.30 g) as a colorless solid.

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in a small amount of methanol
  3. additionafter adding a 4N hydrogen chloride-ethyl acetate solution until the solution
  4. customthe solvent was removed under reduced pressure
  5. additionThe residue was treated with 50 ml of t-butyl methyl ether
  6. filtrationthe solid was collected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-e79227419f194e45becae30b4df55006
Source dataset
uspto-grants-2010_10
Patent number
US07807690B2

Reaction notes

Loading…