Pyridine → 2-Methanesulfonylamino-4,5-diphenylthiazole

HRID 2399538Notes

Reaction equation

HRID 2399538 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[S:8][C:9]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:11]=1.N1C=CC=CC=1>ClCCl>[CH3:1][S:2]([NH:6][C:7]1[S:8][C:9]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:11]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 732222-Amino-4,5-diphenylthiazole

Product 1

HCID 152327792-Methanesulfonylamino-4,5-diphenylthiazoleYield 24.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.5 g of methanesulfonyl chloride was dropped into a solution of 5.0 g of 2-amino-4,5-diphenylthiazole and 3.3 ml of pyridine in dichloromethane under stirring at room temperature, and the resulting mixture was stirred as such overnight. 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 isopropyl ether and ethyl acetate as a developer. The crystals thus obtained were recovered by filtration from isopropyl ether and washed with diethyl ether to give 1.6 g of 2-methanesulfonylamino-4,5-diphenylthiazole. The melting point of this product was from 225° to 227° C.

Workup

  1. stirringthe resulting mixture was stirred as such overnight
  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. filtrationwere recovered by filtration from isopropyl ether
  8. washwashed with diethyl ether

Sources & evidence

ORD record
ord-fdd4fd7aa5ad4fabada383111c203b20
Source dataset
uspto-grants-1995_09
Patent number
US05449783

Reaction notes

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