Trifluoroacetic anhydride → HCID 13987794, compound

HRID 2231685Notes

Reaction equation

HRID 2231685 reaction equation
C(=O)=O.CC(C)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[Cl:21][C:22]1[C:23](=[O:50])[N:24]([CH:47]([CH3:49])[CH3:48])[N:25]=[CH:26][C:27]=1[NH:28][CH2:29][CH:30]([OH:46])[CH2:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]([O:41][CH3:42])=[O:40])=[CH:35][C:34]=1[CH2:43][CH2:44][CH3:45].C(=O)([O-])O.[Na+]>O1CCCC1.C(N(CC)CC)C.CS(C)=O>[Cl:21][C:22]1[C:23](=[O:50])[N:24]([CH:47]([CH3:49])[CH3:48])[N:25]=[CH:26][C:27]=1[NH:28][CH2:29][C:30](=[O:46])[CH2:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]([O:41][CH3:42])=[O:40])=[CH:35][C:34]=1[CH2:43][CH2:44][CH3:45]

Participants

8

Reactant 4

HCID 9845Trifluoroacetic anhydrideHCID 516892Sodium BicarbonateHCID 13987786HCID 13987786, compoundHCID 18522661Acetone cardice

Product 1

HCID 13987794HCID 13987794, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent3×HCID 8471TriethylamineSolvent

Procedure

A mixture of 1.11 g of dimethylsulfoxide and 20 ml of tetrahydrofuran was cooled with dry ice-acetone, and a mixture of 2.24 g of trifluoroacetic anhydride and 3.67 ml of tetrahydrofuran, was gradually dropwise added thereto. The mixture was stirred for 20 minutes, and then a solution obtained by dissolving 0.93 g of 4-chloro-5-[3-(2-n-propyl-4-methoxycarbonylphenoxy)-2-hydroxypropylamino]-2-i-propyl-3(2H)pyridazinone (Compound No. 44) in 8 ml of tetrahydrofuran, was dropwise added thereto. The mixture was stirred for 30 minutes. Then, 1.26 g of triethylamine was dropwise added. Then, the mixture was stirred for 30 minutes under cooling with ice and then for 1 hour at room temperature. Sodium hydrogen carbonate was added thereto, and tetrahydrofuran was distilled off under reduced pressure. The residue was extracted with chloroform, and the extract was washed with water, and dried over sodium sulfate. Then, the solvent was distilled off, and the residue thereby obtained was purified by silica gel column chromatography by using benzene-ethyl acetate (1:1, v/v) as the developer. The solvent was distilled off, and the colorless crystals thereby obtained were further recrystallized from ethyl acetate-ethyl ether to obtain 0.52 g of the above identified compound as colorless crystals having a melting point of 133° C.

Workup

  1. additionwas gradually dropwise added
  2. customa solution obtained
  3. stirringThe mixture was stirred for 30 minutes
  4. stirringThen, the mixture was stirred for 30 minutes
  5. temperatureunder cooling with ice
  6. waitfor 1 hour at room temperature
  7. distillationtetrahydrofuran was distilled off under reduced pressure
  8. extractionThe residue was extracted with chloroform
  9. washthe extract was washed with water
  10. dry with materialdried over sodium sulfate
  11. distillationThen, the solvent was distilled off
  12. customthe residue thereby obtained
  13. customwas purified by silica gel column chromatography
  14. distillationThe solvent was distilled off
  15. customthe colorless crystals thereby obtained
  16. customwere further recrystallized from ethyl acetate-ethyl ether
  17. customto obtain 0.52 g of the

Sources & evidence

ORD record
ord-aae4a92f2edd482a9b8b529fa449ca46
Source dataset
uspto-grants-1988_11
Patent number
US04783462

Reaction notes

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