Triethylamine → HCID 15232777, compound

HRID 2399536Notes

Reaction equation

HRID 2399536 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:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[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:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)=[C:13]([C:15]2[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)[N:14]=1)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62406Trifluoromethanesulfonic acidHCID 14817254,5-Bis(4-methoxyphenyl)-1,3-thiazol-2-amine

Product 1

HCID 15232777HCID 15232777, compoundYield 26.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

13.5 g of anhydrous trifluoromethanesulfonic acid was slowly dropped into a solution of 5.0 g of 2-amino-4,5-bis(4-methoxyphenyl)thiazole and 5.0 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 isopropyl ether/ethyl acetate to give 1.9 g of 2-trifluoromethanesulfonylamino-4,5-bis(4-methoxy-phenyl)thiazole. The melting point of this product was from 240° to 242° 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 isopropyl ether/ethyl acetate

Sources & evidence

ORD record
ord-f11e6a150b6b439c86c140e057d3d1a2
Source dataset
uspto-grants-1995_09
Patent number
US05449783

Reaction notes

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