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Tris(furan-2-yl)phosphane → (7-Cyclohex-1-enyl-4-methoxy-benzothiazol-2-yl)-carbamic acid methyl ester

HRID 1582139
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인쇄 미리보기

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HRID 1582139 반응식
[CH3:1][O:2][C:3](=[O:17])[NH:4][C:5]1[S:6][C:7]2[C:13](I)=[CH:12][CH:11]=[C:10]([O:15][CH3:16])[C:8]=2[N:9]=1.C([Sn](CCCC)(CCCC)[C:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=1)CCC.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[CH3:1][O:2][C:3](=[O:17])[NH:4][C:5]1[S:6][C:7]2[C:13]([C:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=3)=[CH:12][CH:11]=[C:10]([O:15][CH3:16])[C:8]=2[N:9]=1
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참가 물질

6

반응물 3

HCID 521585Tris(furan-2-yl)phosphaneHCID 11783615Stannane, tributyl-1-cyclohexen-1-yl-HCID 60117385(7-Iodo-4-methoxy-benzothiazol-2-yl)-carbamic acid methyl ester

생성물 1

HCID 10193275(7-Cyclohex-1-enyl-4-methoxy-benzothiazol-2-yl)-carbamic acid methyl ester수율 18.6%

시약·촉매·용매 2

HCID 6505921
(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium
촉매
HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

To a stirred solution of 100 mg (0.27 mmol) (7-iodo-4-methoxy-benzothiazol-2-yl)-carbamic acid methyl ester in 3 ml dioxane were added 0.2 g (0.54 mmol) tri-n-butyl-(1-cyclohex-1-enyl)-stannane, 5.0 mg (0.009 mmol) bis(dibenzylideneacetone)palladium and 10 mg (0.043 mmol) trifurylphosphine. The mixture was heated at 100° C. for 16 h and then poured onto water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (ethyl acetate/hexane 1:4) afforded 16 mg (7-Cyclohex-1-enyl-4-methoxy-benzothiazol-2-yl)-carbamic acid methyl ester (18%) as an off white solid; F.p.: 164-173° C.

후처리

  1. additionpoured onto water
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-4c9088f5ede244958118f89c6dd27c92
출처 데이터셋
uspto-grants-2004_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06734179B2

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