Sodium hydride → HCID 13526446, compound

HRID 444292Notes

Reaction equation

HRID 444292 reaction equation
[H-].[Na+].Br.[OH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:18]3[C:14]([S:15][CH2:16][CH2:17]3)=[N:13][C:12]=2[C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)=[CH:7][CH:6]=1.FC(F)(F)S(O[CH2:32][C:33]([F:36])([F:35])[F:34])(=O)=O>O1CCCC1>[F:34][C:33]([F:36])([F:35])[CH2:32][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[N:18]3[C:14]([S:15][CH2:16][CH2:17]3)=[N:13][C:12]=2[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:32][C:33]([F:34])([F:35])[F:36])=[CH:21][CH:20]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 13526440HCID 13526440, compound

Product 1

HCID 13526446HCID 13526446, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 6.14 g. of sodium hydride [50% dispersion in oil, (0.128 mole)] in 150 ml. of tetrahydrofuran (distilled from lithium aluminum hydride) at 0° C. under nitrogen was added 10.0 g. (0.0256 mole) of 5,6-bis(p-hydroxyphenyl)-2,3-dihydroimidazo[2,1-b]thiazole hydrobromide. After 30 minutes, 17.82 g. (0.0768 mole) of 2,2,2-trifluoroethyl trifluoromethanesulfonate was added dropwise, maintaining the temperature below 0° C. After stirring overnight at room temperature, the suspension was added portionwise to 500 ml. of ice water under nitrogen and extracted three times with methylene chloride. The organic layer was washed with water, dried over potassium carbonate and concentrated in vacuo. The residue was recrystallized from methylene chloride-hexane to give 5,6-bis[p-(2,2,2-trifluoroethoxy)phenyl]-2,3-dihydroimidazo[2,1-b]thiazole, m.p. 163°-164° C.

Workup

  1. additionTo a stirred suspension of 6.14 g
  2. temperaturemaintaining the temperature below 0° C
  3. additionthe suspension was added portionwise to 500 ml
  4. extractionof ice water under nitrogen and extracted three times with methylene chloride
  5. washThe organic layer was washed with water
  6. dry with materialdried over potassium carbonate
  7. concentrationconcentrated in vacuo
  8. customThe residue was recrystallized from methylene chloride-hexane

Sources & evidence

ORD record
ord-e98623e4685649508dd9134edf15e264
Source dataset
uspto-grants-1981_04
Patent number
US04263311

Reaction notes

Loading…