Dimethylamine → [2-[3-(4-Bromo-phenyl)-benzo[d]isothiazol-6-yloxy]-ethyl]-dimethyl-amine

HRID 966169Notes

Reaction equation

HRID 966169 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:20]=[CH:19][C:8]2[C:9]([C:12]3[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=3)=[N:10][S:11][C:7]=2[CH:6]=1.[CH3:21][NH:22][CH3:23].C([O-])(O)=O.[Na+]>CC(N(C)C)=O.C(O)C.CCOCC>[Br:18][C:15]1[CH:16]=[CH:17][C:12]([C:9]2[C:8]3[CH:19]=[CH:20][C:5]([O:4][CH2:3][CH2:2][N:22]([CH3:23])[CH3:21])=[CH:6][C:7]=3[S:11][N:10]=2)=[CH:13][CH:14]=1

Participants

7

Reactant 3

HCID 674DimethylamineHCID 516892Sodium BicarbonateHCID 22314138HCID 22314138, compound

Product 1

HCID 22314199[2-[3-(4-Bromo-phenyl)-benzo[d]isothiazol-6-yloxy]-ethyl]-dimethyl-amineYield 92.8%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 31374DimethylacetamideSolvent

Procedure

75 mg (0.18 mmol) 6-(2-Bromo-ethoxy)-3-(4-bromo-phenyl)-benzo[d]isothiazole in 2.5 ml DMA were treated with 98 μl (0.54 mmol, 3eq) 5.6 M N,N-dimethylamine in ethanol for 35 h at RT. The solution was diluted with ether and a saturated aqueous solution of NaHCO3. The inorganic phase was extracted with ether, the combined organic phases were washed with brine and dried over Na2SO4. Column chromatography on silica gel with CH2Cl2:MeOH 8:1 yielded 63 mg (92%) [2-[3-(4-Bromo-phenyl)-benzo[d]isothiazol-6-yloxy]-ethyl]-dimethyl-amine as colorless oil, MS: 377(MH+, 1Br).

Workup

  1. extractionThe inorganic phase was extracted with ether
  2. washthe combined organic phases were washed with brine
  3. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-ed8867c570eb4bf0bc5e8ba2c094b864
Source dataset
uspto-grants-2005_10
Patent number
US06951879B2

Reaction notes

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