Triethylamine → HCID 15232778, compound

HRID 2399537Notes

Reaction equation

HRID 2399537 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][C:25]([F:28])=[CH:24][CH:23]=2)=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([F: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:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)=[C:13]([C:15]2[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=2)[N:14]=1)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62406Trifluoromethanesulfonic acidHCID 19385956HCID 19385956, compound

Product 1

HCID 15232778HCID 15232778, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2.68 ml of anhydrous trifluoromethanesulfonic acid was slowly dropped into a solution of 2.88 g of 2-amino-4,5-bis(4-fluorophenyl)thiazole and 1.8 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 1 hour. Then the reaction mixture was successively washed with diluted hydrochloric acid, a 5% 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 isopropyl ether as a developer. The crystals thus obtained were recrystallized from petroleum ether/diethyl ether to give 0.47 g of 2-trifluoromethanesulfonylamino-4,5-bis(4-fluorophenyl)thiazole. The melting point of this product was from 193° to 195° C.

Workup

  1. stirringthe resulting mixture was stirred as such for 1 hour
  2. washThen the reaction mixture was successively washed with diluted hydrochloric acid
  3. dry with materiala 5% 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 petroleum ether/diethyl ether

Sources & evidence

ORD record
ord-a36f0bc63c3b4246941b38241168cd6e
Source dataset
uspto-grants-1995_09
Patent number
US05449783

Reaction notes

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