Toluene → HCID 178469938, compound

HRID 1161504Notes

Reaction equation

HRID 1161504 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 solution of 3.30 g of 3-(N′-t-butoxycarbonylhydrazino)-1H-pyrazole-4-carboxylic acid ethyl ester in 50 ml of 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 solution containing hydrochloric acid in ethyl acetate until the solution reached acidic, the solvent was removed under reduced pressure. The residue was treated with 50 ml of t-butyl methyl ether, and the solid was filtered off and dried under reduced pressure to give the title compound (3.30 g) as a white 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 solution
  4. additioncontaining hydrochloric acid in ethyl acetate until the solution
  5. customthe solvent was removed under reduced pressure
  6. additionThe residue was treated with 50 ml of t-butyl methyl ether
  7. filtrationthe solid was filtered off
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-34fb8ef4ab7d4f598a9f62230e6b8984
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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