t-Butyl 4-Fluoroacetoacetate → HCID 178516166, compound

HRID 1111270Notes

Reaction equation

HRID 1111270 reaction equation
[F:1][CH2:2][C:3](=O)[CH2:4][C:5]([O:7]C(C)(C)C)=O.[NH2:13][C:14]1[N:18]=[C:17]([S:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[NH:16][N:15]=1>C(O)(=O)C>[CH2:20]([S:19][C:17]1[N:18]=[C:14]2[N:13]=[C:3]([CH2:2][F:1])[CH:4]=[C:5]([OH:7])[N:15]2[N:16]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 15029427t-Butyl 4-FluoroacetoacetateHCID 178509291HCID 178509291, compound

Product 1

HCID 178516166HCID 178516166, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution containing 20.0 g (114 mmol) of t-butyl 4-fluoroacetoacetate, 23.4 g (114 mmol) of 3-amino-5-benzylthio-1,2,4-triazole in 250 ml of glacial acetic acid was heated at reflux with stirring for 5.5 hr and then allowed to cool and stand overnight. The crystals that formed were ground to reduce their size and then recovered by filtration and dried in a vacuum oven to obtain 18.3 g (55 percent of theory) of the title product as a white powder melting with decomposition at 214°-218° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. temperatureto cool
  4. waitstand overnight
  5. customThe crystals that formed
  6. filtrationrecovered by filtration
  7. customdried in a vacuum oven

Sources & evidence

ORD record
ord-5ee8dab487404f6e8e34b3a1d2f23b71
Source dataset
uspto-grants-1990_12
Patent number
US04979981

Reaction notes

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