Chlorosuccinimide → 7-Chloro-2-(methylthio)benzo[d]thiazol-6-ol

HRID 1922269Notes

Reaction equation

HRID 1922269 reaction equation
[CH3:1][S:2][C:3]1[S:4][C:5]2[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:6]=2[N:7]=1.[Cl:13]N1C(=O)CCC1=O>CN1C(=O)CCC1.C(=O)(O)[O-].[Na+]>[Cl:13][C:11]1[C:5]2[S:4][C:3]([S:2][CH3:1])=[N:7][C:6]=2[CH:8]=[CH:9][C:10]=1[OH:12]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 450774142-(Methylthio)benzo[d]thiazol-6-ol

Product 1

HCID 577255217-Chloro-2-(methylthio)benzo[d]thiazol-6-olYield 48.3%

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To the solution of 2-(methylthio)benzo[d]thiazol-6-ol (500 mg, 2.53 mmol, 1.0 eq) in 10 mL of NMP was added N-chlorosuccinimide (507 mg, 3.80 mmol, 1.5 eq) at room temperature. The reaction mixture was stirred at room temperature for 1 hour thereafter the mixture was diluted with saturated sodium bicarbonate solution (ca. 100 mL) and aqueous layer extracted with DCM (ca. 150 mL×3). Combined organic layers were dried over sodium sulfate, filtered and condensed under reduced pressure. Purification on ISCO using gradient 0%-100% ethyl acetate-hexane gave 283.39 mg of product in 48% yields structure of which was confirmed by H+NMR. LC/MS (m/z) [232.0] (MH+)

Workup

  1. extractionextracted with DCM (ca. 150 mL×3)
  2. dry with materialCombined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. customcondensed under reduced pressure
  5. customPurification on ISCO

Sources & evidence

ORD record
ord-70a84ee9da4946f7949537561802d592
Source dataset
uspto-grants-2012_05
Patent number
US08173689B2

Reaction notes

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