Sodium hydride → 4-Bromo-2-n-butylmercapto-6-methylbenzothiazole

HRID 1769023Notes

Reaction equation

HRID 1769023 reaction equation
[Br:1][C:2]1[C:7]2[N:8]=[C:9]([SH:11])[S:10][C:6]=2[CH:5]=[C:4]([CH3:12])[CH:3]=1.[H-].[Na+]>O1CCCC1>[Br:1][C:2]1[C:7]2[N:8]=[C:9]([S:11][CH2:7][CH2:2][CH2:3][CH3:4])[S:10][C:6]=2[CH:5]=[C:4]([CH3:12])[CH:3]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 178422422HCID 178422422, compound

Product 1

HCID 544229414-Bromo-2-n-butylmercapto-6-methylbenzothiazoleYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 10 ml of tetrahydrofuran solution containing 0.52 g of 4-bromo-2-mercapto-6-methylbenzothiazole was added 50 mg of sodium hydride at 0° C. After adding 0.28 g of n-bromobutane, the whole mixture was refluxed for 2 hours, distilled under reduced pressure to remove tetrahydrofuran and then extracted with ethyl acetate by adding water and ethyl acetate. The ethyl acetate layer was dried with anhydrous sodium sulfate and evaporated under reduced pressure to obtain the title compound in a yellow liquid state (Yield: 66%).

Workup

  1. temperaturethe whole mixture was refluxed for 2 hours
  2. distillationdistilled under reduced pressure
  3. customto remove tetrahydrofuran
  4. extractionextracted with ethyl acetate
  5. additionby adding water and ethyl acetate
  6. dry with materialThe ethyl acetate layer was dried with anhydrous sodium sulfate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5fed2a69386d4b689cfa1124dc96875f
Source dataset
uspto-grants-1995_01
Patent number
US05380735

Reaction notes

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