Phosgene → N-(2,2,3,3-tetrafluorobenzofuran-5-yl)-3-(4-difluoromethoxyphenyl)-4-phenylpyrazoline-1-carboxamide

HRID 568948Notes

Reaction equation

HRID 568948 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([F:11])([F:10])[C:7]([F:13])([F:12])[C:6]=2[CH:14]=1.[C:15](Cl)(Cl)=[O:16].[F:19][CH:20]([F:39])[O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[NH:29][NH:30][CH2:31][C:32]=2[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:24][CH:23]=1>C1(C)C=CC=CC=1.C(OCC)C.C(N(CC)CC)C>[F:11][C:8]1([F:10])[C:7]([F:13])([F:12])[C:6]2[CH:14]=[C:2]([NH:1][C:15]([N:30]3[CH2:31][C:32]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)=[C:28]([C:25]4[CH:24]=[CH:23][C:22]([O:21][CH:20]([F:19])[F:39])=[CH:27][CH:26]=4)[NH:29]3)=[O:16])[CH:3]=[CH:4][C:5]=2[O:9]1

Participants

7

Reactant 3

HCID 6371PhosgeneHCID 137849875-Benzofuranamine, 2,2,3,3-tetrafluoro-2,3-dihydro-HCID 704081453-(4-Difluoromethoxyphenyl)-4-phenylpyrazoline

Product 1

HCID 86742033N-(2,2,3,3-tetrafluorobenzofuran-5-yl)-3-(4-difluoromethoxyphenyl)-4-phenylpyrazoline-1-carboxamide

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 1140TolueneSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 0.75 g (0.0036 mole) of the 5-amino-2,2,3,3-tetrafluorobenzofuran of part A, dissolved in 109 ml of toluene, was added dropwise to a stirred solution of 8.0 ml 20% phosgene in toluene. After complete addition the mixture was heated at reflux for two hours. The mixture was cooled and the solvent removed by evaporation under reduced pressure leaving a residue. This residue was dissolved in 15 ml of diethyl ether and added to a stirred solution of 1.04 g (0.0036 mole) 3-(4-di-fluoromethoxyphenyl)-4-phenylpyrazoline and three drops of tri-ethylamine in 100 ml of diethyl ether. After complete addition the mixture was heated at reflux for one hour, then cooled to room temperature and stirred for approximately 18 hours. The solvent was removed from the reaction mixture by evaporation under reduced pressure leaving a solid residue. Recrystallization from ethanol provided 0.99 g of N-(2,2,3,3-tetrafluorobenzofuran-5-yl)-3-(4-difluoromethoxyphenyl)-4-phenylpyrazoline-1-carboxamide (mp 155°-159° C.). The nmr spectrum and elemental analysis were consistent with the proposed structure.

Workup

  1. additionAfter complete addition the mixture
  2. temperaturewas heated
  3. temperatureat reflux for two hours
  4. temperatureThe mixture was cooled
  5. customthe solvent removed by evaporation under reduced pressure
  6. customleaving a residue
  7. additionAfter complete addition the mixture
  8. temperaturewas heated
  9. temperatureat reflux for one hour
  10. customThe solvent was removed from the reaction mixture by evaporation under reduced pressure
  11. customleaving a solid residue
  12. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-14e71865f79f4aaa85aabad87dafc68b
Source dataset
uspto-grants-1988_03
Patent number
US04730062

Reaction notes

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