Ethyl Acetate → HCID 118223428, compound

HRID 2200138Notes

Reaction equation

HRID 2200138 reaction equation
C(=O)(O)[O-].[Na+].[N:6]#[C:7]Br.[NH2:9][C:10]1[CH:11]=[C:12]([CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=1)[C:13]([NH:15][NH2:16])=[O:14].CCOC(C)=O>C(O)C>[NH2:9][C:10]1[CH:11]=[C:12]([C:13]2[O:14][C:7]([NH2:6])=[N:16][N:15]=2)[CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 90020746HCID 90020746, compound

Product 1

HCID 118223428HCID 118223428, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add sodium bicarbonate (270 mg, 3.21 mmol) and cyanogen bromide (187 mg, 1.76 mmol) to the solution of 3-amino-5-(trifluoromethyl)benzohydrazide (400 mg, 1.6 mmol) in ethanol (5 mL), reflux for 5 hrs. TLC (PE:EtOAc=1:1) shows the reaction is complete. Concentrate the mixture, partition the residue between EtOAc and water, collect the organic layer, wash with saturated sodium bicarbonate solution, dry over anhydrous sodium sulfate, and concentrate under reduced pressure to afford the crude product. Recrystallization in ethyl acetate yields the pure product (280 mg, 63%).

Workup

  1. temperaturereflux for 5 hrs
  2. concentrationConcentrate the mixture
  3. custompartition the residue between EtOAc and water
  4. customcollect the organic layer
  5. washwash with saturated sodium bicarbonate solution
  6. dry with materialdry over anhydrous sodium sulfate
  7. concentrationconcentrate under reduced pressure
  8. customto afford the crude product
  9. customRecrystallization in ethyl acetate

Sources & evidence

ORD record
ord-96963abb2ab34beb9428dc1edc53f95a
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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