Benzyl mercaptan → 2-(Benzylthio)-5-bromothiazole

HRID 2036853Notes

Reaction equation

HRID 2036853 reaction equation
Br[C:2]1[S:3][C:4]([Br:7])=[CH:5][N:6]=1.C([O-])([O-])=O.[K+].[K+].[CH2:14]([SH:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C=O)C.O>[CH2:14]([S:21][C:2]1[S:3][C:4]([Br:7])=[CH:5][N:6]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 7509Benzyl mercaptanHCID 11430Potassium CarbonateHCID 3123942,5-Dibromothiazole

Product 1

HCID 670559942-(Benzylthio)-5-bromothiazoleYield 97.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 2,5-dibromothiazole (2.0 g, 8.23 mmol) in DMF (15 mL) was added K2CO3 (1.16 g, 8.40 mmol) followed by benzyl mercaptan (1.07 g, 8.40 mmol) in DMF (10 mL) over a period of 20 min. The reaction mixture was stirred at RT for over night. After this time, the reaction mixture was diluted with water and extracted in EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting crude product was purified by silica gel chromatography (0.2% EtOAc in hexane) to yield 2-(benzylthio)-5-bromothiazole (2.3 g, 97.5% yield) as a brown solid. 1H NMR (400 MHz, DMSO-d6, δ): 7.56 (s, 1H); 7.25-7.36 (m, 5H); 4.39 (s, 2H). 1H LCMS Method V: Retention time 2.319 min, [M+1]=286.

Workup

  1. extractionextracted in EtOAc
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting crude product was purified by silica gel chromatography (0.2% EtOAc in hexane)

Sources & evidence

ORD record
ord-bf8783dd04b3493d87bb262b29735afb
Source dataset
uspto-grants-2013_11
Patent number
US08575184B2

Reaction notes

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