Potassium Carbonate → HCID 8829822, compound

HRID 333916Notes

Reaction equation

HRID 333916 reaction equation
Br[C:2]1[S:6][C:5]([NH2:7])=[N:4][CH:3]=1.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([SH:16])=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([S:16][C:2]2[S:6][C:5]([NH2:7])=[N:4][CH:3]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 127654-MethoxybenzenethiolHCID 436002-Thiazolamine, 5-bromo-

Product 1

HCID 8829822HCID 8829822, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-bromo-thiazol-2-ylamine (70a, 10.0 g, 38.5 mmol), 4-methoxy-benzenethiol (4.70 ml, 38.5 mmol) and K2CO3 (21.0 g, 151 mmol) in DMF (100 mL) was heated at 80° C. for 1.0 hour and stirred further 16 hours at room temperature. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4(s), and concentrated under reduced pressure to give 5-(4-methoxy-phenylsulfanyl)-thiazol-2-ylamine (70b, 6.70 g).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4(s)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ac8f5bc462b1470b82b878f2273f12a0
Source dataset
uspto-grants-2014_11
Patent number
US08883793B2

Reaction notes

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