Thiophenol → (+/-) trans 1-(Phenylthio)-2-ethoxycarbonylaminoindane

HRID 965210노트

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HRID 965210 반응식
[CH2:1]([O:3][C:4]1[O:5][C@H:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][C@H:7]2[N:8]=1)[CH3:2].[C:16]1([SH:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1.C(OCC)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:16]1([S:22][C@@H:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][C@H:7]2[NH:8][C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

6

반응물 2

HCID 7969ThiophenolHCID 18661302(3AR,8bS)-2-ethoxy-4,8b-dihydro-3aH-indeno[2,1-d]oxazole

생성물 1

HCID 54176936(+/-) trans 1-(Phenylthio)-2-ethoxycarbonylaminoindane수율 89.3%

시약·촉매·용매 3

HCID 521998p-Toluenesulfonic acid monohydrate촉매HCID 1140Toluene용매HCID 3283Diethyl Ether용매

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온도
60 °C

실험 절차

A solution of (±) cis-2-ethoxy-3a,8b-dihydro-4H-indeno[2,1-d]oxazole (1.0 g, 0.005 mol) in dry toluene (5 ml) was treated with thiophenol (0.55 g, 0.005 mol) and a catalytic amount of p-toluenesulfonic acid monohydrate (25 mg). The mixture was heated at 60° C. for 2 h and then at 80° C. for a further 5 h. The reaction was diluted with diethyl ether and washed with 5% NaOH (3×10 ml) followed by water (10 ml) and brine (10 ml). The organic phase was dried over Na2SO4 and concentrated in vacuo to give an oil (1.4 g) which was purified on a silica gel column using CH2Cl2 as eluant. Pooling of fractions containing the major slower running component afforded the title compound as a colourless solid (0.74 g), m.p. 60.5°-62° C. (from n-pentane/diethyl ether).

후처리

  1. washwashed with 5% NaOH (3×10 ml)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-1f99f6bc7a1d421798b66d12d2dcb664
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05773463

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