Pyridine → HCID 57551218, compound

HRID 1644652Notes

Reaction equation

HRID 1644652 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.N1C=CC=CC=1.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[C:16]([C:24]#[N:25])[CH:15]=1>>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([NH:1][C:2]2[S:3][CH:4]=[CH:5][N:6]=2)(=[O:21])=[O:22])=[C:16]([C:24]#[N:25])[CH:15]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 21552-AminothiazoleHCID 179783774-Bromo-2-cyanobenzenesulfonyl chloride

Product 1

HCID 57551218HCID 57551218, compoundYield 7.3%

Procedure

To 2-AMINOTHIAZOLE (0.21 g, 0.0021 mol) in Pyridine (1 mL, 0.01 mol) was added portion-wise the crude 4-Bromo-2-cyano-benzenesulfonyl chloride (0.40 g, 0.0014 mol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, diluted with Ethyl acetate, washed with 1.0 N HCl, H2O and brine, dried with anhydrous sodium sulfate, filtered and concentrated to give the crude product, which was purified on ISCO (25% to 100% Ethyl acetate in hexanes). 35 mg of the product was obtained as a light yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with Ethyl acetate
  3. washwashed with 1.0 N HCl, H2O and brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude product, which
  8. customwas purified on ISCO (25% to 100% Ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-f91bcbd577f6492595c2a6b53e56d25f
Source dataset
uspto-grants-2012_02
Patent number
US08124610B2

Reaction notes

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