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Sodium Carbonate → N1-(5-Phenylbenzo[d]isothiazol-3-yl)propane-1,3-diamine

HRID 502562
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인쇄 미리보기

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HRID 502562 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[S:9][N:8]=[C:7]([NH:10][CH2:11][CH2:12][CH2:13][NH2:14])[C:6]=2[CH:15]=1.[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(Cl)Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:16]1([C:2]2[CH:3]=[CH:4][C:5]3[S:9][N:8]=[C:7]([NH:10][CH2:11][CH2:12][CH2:13][NH2:14])[C:6]=3[CH:15]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1
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참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 58726901N1-(5-bromobenzo[d]isothiazol-3-yl)propane-1,3-diamine

생성물 1

HCID 58727100N1-(5-Phenylbenzo[d]isothiazol-3-yl)propane-1,3-diamine

시약·촉매·용매 4

HCID 74236Tetrabutylammonium Bromide촉매
HCID 167845
palladium(II) acetate
촉매
HCID 962Water용매
HCID 6344Dichloromethane용매

실험 절차

A mixture of N1-(5-bromobenzo[d]isothiazol-3-yl)propane-1,3-diamine (100 mg, 0.35 mmol), phenylboronic acid (43 mg, 0.35 mmol), tetrabutylammonium bromide (115 mg, 0.35 mmol), sodium carbonate (110 mg, 1.05 mmol) and palladium (II) acetate (1 mg) in water (3 mL) was microwaved at 150° C. for 5 min. The reaction was diluted with methylene chloride and the mixture was washed successively with aqueous sodium bicarbonate and brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting product, N1-(5-Phenylbenzo[d]isothiazol-3-yl)propane-1,3-diamine, was carried forward without further purification. MW=238 confirmed by LC-MS, tr=2.73 min (Method B) MH+=237-239

후처리

  1. customwas microwaved at 150° C. for 5 min
  2. washthe mixture was washed successively with aqueous sodium bicarbonate and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting product, N1-(5-Phenylbenzo[d]isothiazol-3-yl)propane-1,3-diamine, was carried forward without further purification
  7. customconfirmed by LC-MS, tr=2.73 min (Method B) MH+=237-239

출처 및 근거

ORD 기록
ord-07fa30e7e9be4e9c974381d6be3e0cf9
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07776847B2

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