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

HRID 966169ノート

反応式

HRID 966169 の反応式
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

参加物

7

反応物 3

HCID 674DimethylamineHCID 516892Sodium BicarbonateHCID 22314138HCID 22314138、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 3283Diethyl Ether溶媒HCID 31374Dimethylacetamide溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-ed8867c570eb4bf0bc5e8ba2c094b864
出典データセット
uspto-grants-2005_10
特許番号
US06951879B2

反応ノート

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