Benzyl Chloride → 2-Benzylsulfanyl-benzothiazole

HRID 1029328Notes

Reaction equation

HRID 1029328 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[SH:9][C:10]1[S:11][C:12]2[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=2[N:14]=1.[OH-].[Na+]>C(O)C.O>[CH2:1]([S:9][C:10]1[S:11][C:12]2[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=2[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 14798Sodium HydroxideHCID 178418395HCID 178418395, compound

Product 1

HCID 4974652-Benzylsulfanyl-benzothiazoleYield 68.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of 28.1 g (0.2 mol) of benzyl chloride in 50 ml of ethanol is added slowly, with stirring, to a solution of 33.4 g (0.2 mol) of 2-mercaptobenzothiazole and 8 g (0.2 mol) of NaOH in 150 ml of ethanol and 25 ml of water. The resulting solution is refluxed for 2.5 h. After cooling, it is filtered and evaporated to leave 35.1 g of a yellowish solid melting at 39°-40° C. 1H NMR (CDCl3): δ4.41 (2H), δ6.98-7.8 (9H) ppm.

Workup

  1. temperatureThe resulting solution is refluxed for 2.5 h
  2. temperatureAfter cooling
  3. filtrationit is filtered
  4. customevaporated

Sources & evidence

ORD record
ord-41ee070a13da4a1c9a4bd6a06ceff585
Source dataset
uspto-grants-1992_04
Patent number
US05102457

Reaction notes

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