Triethylamine → HCID 21831305, compound

HRID 363453Notes

Reaction equation

HRID 363453 reaction equation
[F:1][C:2]([F:29])([C:7]1[CH:8]=[CH:9][C:10]2[O:15][C:14]([CH2:18][F:19])([CH2:16][F:17])[C@@H:13](O)[C@H:12]([N:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]3=[O:27])[C:11]=2[CH:28]=1)[C:3]([F:6])([F:5])[F:4].CS(Cl)(=O)=O.C(N(CC)CC)C>O1CCCC1>[F:29][C:2]([F:1])([C:7]1[CH:8]=[CH:9][C:10]2[O:15][C:14]([CH2:18][F:19])([CH2:16][F:17])[CH:13]=[C:12]([N:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]3=[O:27])[C:11]=2[CH:28]=1)[C:3]([F:6])([F:5])[F:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 44329937HCID 44329937, compound

Product 1

HCID 21831305HCID 21831305, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.15 g of trans-6-pentafluoroethyl-2,2-bisfluoromethyl-3,4-dihydro-4-(1,2-dihydro-2-oxo-1-pyridyl)-2H-1-benzopyran-3-ol, 0.07 g of methanesulfonyl chloride, 0.08 g of triethylamine and 10 ml of tetrahydrofuran was stirred at room temperature for 8 hours and the solvent was distilled off. Water was added thereto and the mixture was extracted with methylene chloride. After the organic layer was washed with water and dried, the solvent was distilled off. The resultant residue was dissolved in 4 ml of tetrahydrofuran and 0.06 g of sodium hydrate (60%) was added thereto with stirring under ice-cooling. The mixture was then stirred at room temperature for 66 hours. Ice water was added thereto and the mixture was extracted with methylene chloride. After the organic layer was washed with water and dried, the solvent was distilled off. The resultant residue was purified using silica gel column chromatography (developing solution, MeOH:CH2Cl2 =1:99) to obtain 0.09 g of 6-pentafluoroethyl-2,2-bisfluoromethyl-4-(1,2-dihydro-2-oxo-1-pyridyl)-2H-1-benzopyran represented by the following formula having a melting point of 137°-138° C.

Workup

  1. distillationthe solvent was distilled off
  2. additionWater was added
  3. extractionthe mixture was extracted with methylene chloride
  4. washAfter the organic layer was washed with water
  5. customdried
  6. distillationthe solvent was distilled off
  7. dissolutionThe resultant residue was dissolved in 4 ml of tetrahydrofuran
  8. addition0.06 g of sodium hydrate (60%) was added
  9. stirringwith stirring under ice-
  10. temperaturecooling
  11. stirringThe mixture was then stirred at room temperature for 66 hours
  12. additionIce water was added
  13. extractionthe mixture was extracted with methylene chloride
  14. washAfter the organic layer was washed with water
  15. customdried
  16. distillationthe solvent was distilled off
  17. customThe resultant residue was purified

Sources & evidence

ORD record
ord-b93a2dc9f1d64545864804128fd6078b
Source dataset
uspto-grants-1999_02
Patent number
US05874446

Reaction notes

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