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

HRID 270258노트

반응식

HRID 270258 반응식
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

참가 물질

7

반응물 3

HCID 674DimethylamineHCID 516892Sodium BicarbonateHCID 22314138HCID 22314138, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 702Ethanol용매HCID 3283Diethyl Ether용매HCID 31374Dimethylacetamide용매

실험 절차

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, 3 eq) 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).

후처리

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

출처 및 근거

ORD 기록
ord-4531aa915baa4c78b8e1b1097564d38c
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449483B2

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