2,2,2-Trifluoroethanol → HCID 12906276, compound

HRID 127911Notes

Reaction equation

HRID 127911 reaction equation
[Cl:1][C:2]1[C:11]([Cl:12])=[N:10][C:9]2[C:4](=[CH:5][C:6]([Cl:17])=[C:7]([S:13](Cl)(=[O:15])=[O:14])[CH:8]=2)[N:3]=1.[F:18][C:19]([F:23])([F:22])[CH2:20][OH:21].C(N(CC)C(C)C)(C)C>O1CCCC1.C(OCC)C>[Cl:1][C:2]1[C:11]([Cl:12])=[N:10][C:9]2[C:4](=[CH:5][C:6]([Cl:17])=[C:7]([S:13]([O:21][CH2:20][C:19]([F:23])([F:22])[F:18])(=[O:15])=[O:14])[CH:8]=2)[N:3]=1

Participants

6

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 81531DiisopropylethylamineHCID 12906275HCID 12906275, compound

Product 1

HCID 12906276HCID 12906276, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 470 g (1.42 mole) of 2,3,7-trichloro-6-quinoxalinesulfonyl chloride and 153 g (1.53 mole) of 2,2,2-trifluoroethanol in 3 liters of anhydrous tetrahydrofuran are added 183 g (1.42 mole) of N,N-diisopropylethylamine. The resulting mixture is heated under reflux with exclusion of moisture for 24 hours. The solvent is removed under reduced pressure to obtain a residue which is dispersed in one liter of diethyl ether. The resulting mixture is washed twice with 500 ml of water then dried over magnesium sulfate, and filtered. The filtrate obtained therefrom is evaporated to give crude product which is recrystallized first from cyclohexane and then from 2-propanol to give 112 g (20%) of nearly colorless crystals having a melting point of 142°-144°.

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureunder reflux with exclusion of moisture for 24 hours
  3. customThe solvent is removed under reduced pressure
  4. customto obtain a residue which
  5. washThe resulting mixture is washed twice with 500 ml of water
  6. dry with materialthen dried over magnesium sulfate
  7. filtrationfiltered
  8. customThe filtrate obtained
  9. customtherefrom is evaporated
  10. customto give crude product which
  11. customis recrystallized first from cyclohexane
  12. customfrom 2-propanol to give 112 g (20%) of nearly colorless crystals

Sources & evidence

ORD record
ord-e7efe5bf9ad64393998762b0a3167b43
Source dataset
uspto-grants-1981_03
Patent number
US04258044

Reaction notes

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