Triethylamine → HCID 15295285, compound

HRID 2399535Notes

Reaction equation

HRID 2399535 reaction equation
[F:1][C:2]([F:8])([F:7])[S:3](O)(=[O:5])=[O:4].[NH2:9][C:10]1[S:11][C:12]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[N:14]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[F:1][C:2]([F:8])([F:7])[S:3]([NH:9][C:10]1[S:11][C:12]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[C:13]([C:15]2[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=2)[N:14]=1)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62406Trifluoromethanesulfonic acidHCID 2054479HCID 2054479, compound

Product 1

HCID 15295285HCID 15295285, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

15.9 g of anhydrous trifluoromethanesulfonic acid was slowly dropped into a solution of 5.0 g of 2-amino-4-(4-methylphenyl)-5-phenylthiazole and 5.2 ml of triethylamine in chloroform under stirring in a nitrogen atmosphere at -20° to -15° C., and the resulting mixture was stirred as such for 2 hours. Then the reaction mixture was successively washed with diluted hydrochloric acid, a saturated aqueous solution of sodium hydrogencarbonate and water in this order and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the reaction product was separated with a silica gel column by using chloroform/ethyl acetate as a developer. The crystals thus obtained were recrystallized from n-hexane/isopropyl ether/ethyl acetate to give 2.8 g of 2-trifluoromethanesulfonylamino-4-(4-methylphenyl)-5-phenylthiazole. The melting point of this product was from 186.5° to 188.5° C.

Workup

  1. stirringthe resulting mixture was stirred as such for 2 hours
  2. washThen the reaction mixture was successively washed with diluted hydrochloric acid
  3. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and water in this order and dried over anhydrous magnesium sulfate
  4. distillationAfter distilling off the solvent under reduced pressure
  5. customthe reaction product was separated with a silica gel column
  6. customThe crystals thus obtained
  7. customwere recrystallized from n-hexane/isopropyl ether/ethyl acetate

Sources & evidence

ORD record
ord-4ed04b01825641999ceda31882016021
Source dataset
uspto-grants-1995_09
Patent number
US05449783

Reaction notes

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