Potassium Carbonate → HCID 12096239, compound

HRID 2120096Notes

Reaction equation

HRID 2120096 reaction equation
[H-].[Na+].CC([CH:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[C:15]([Br:16])[C:10]=2[S:9](=[O:18])(=[O:17])[N:8]1[C:19]([O-])=O)(C)C.Br.[CH2:23]([N:25]([CH2:28]CBr)[CH2:26][CH3:27])[CH3:24].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[Br:16][C:15]1[C:10]2[S:9](=[O:17])(=[O:18])[N:8]([CH2:19][CH2:28][N:25]([CH2:26][CH3:27])[CH2:23][CH3:24])[CH2:7][C:11]=2[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 706072-Bromoethyldiethylammonium bromideHCID 86587420HCID 86587420, compound

Product 1

HCID 12096239HCID 12096239, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To sodium hydride (90 mg, 2.3 mmol) in tetrahydrofuran (10 mL) at 0° C. was added 1,1-dimethylethyl-7-bromo-1,2-benzisothiazole-2(3H)-carboxylate 1,1-dioxide (0.36 g, 1.5 mmol). The reaction was stirred for 20 min and treated with N,N-diethylaminoethyl bromide hydrobromide (0.39 g, 1.5 mmol) and potassium carbonate (0.62 g, 4.5 mmol). The resulting mixture was stirred at ambient temperature over 18 h, poured into ice water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated in vacuo. The crude material was purified by a flush chromatography (methanol/methylene chloride, 1:9) to afford 7-bromo-N,N-diethyl-1,2-benzisothiazole-2(3H)-ethanamine 1,1-dioxide (0.48 g, 93%). LRMS (ES+): 348.0 (M+H)+.

Workup

  1. stirringThe resulting mixture was stirred at ambient temperature over 18 h
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by a flush chromatography (methanol/methylene chloride, 1:9)

Sources & evidence

ORD record
ord-1876ba8b8a1648888b6b635b63ef6461
Source dataset
uspto-grants-2004_02
Patent number
US06689770B2

Reaction notes

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