N-bromobutanimide → HCID 23148836, compound

HRID 2370557Notes

Reaction equation

HRID 2370557 reaction equation
[Cl:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.[Br:13]N1C(=O)CCC1=O>CN1C(=O)CCC1.O>[Br:13][C:10]1[C:4]2[S:3][C:2]([Cl:1])=[N:6][C:5]=2[CH:7]=[CH:8][C:9]=1[O:11][CH3:12]

Participants

5

Reactant 2

HCID 67184N-bromobutanimide2×HCID 2731322-Chloro-6-methoxybenzothiazole

Product 1

HCID 23148836HCID 23148836, compoundYield 120.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To the solution of 2-chloro-6-methoxy-benzothiazole (200 mg, 1.0 mmol, 1.0 eq) in 5 mL of NMP was added N-bromosuccinimide (213 mg, 1.20 mmol, 1.2 eq) at room temperature. The reaction mixture was stirred at 75° C. for >24 hours with subsequent addition of NBS in small batches for reaction progress, thereafter the mixture was diluted with water (ca. 100 mL) and aqueous layer extracted with ethyl acetate (ca. 150 mL×3). Combined organic layers were dried over sodium sulfate, filtered and condensed under reduced pressure. Purification on ISCO using gradient 0%-50% ethyl acetate-hexane gave 336 mg of product as off white fluffy powder in 60% yields structure of which was confirmed by H+NMR. LC/MS (m/z) [279.9] (MH+)

Workup

  1. extractionextracted with ethyl acetate (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-d79b9ffbb18f434a95c2f0a7cbf06901
Source dataset
uspto-grants-2014_04
Patent number
US08710048B2

Reaction notes

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