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2,4,5-Trichlorophenol → HCID 67799125, 화합물

HRID 1708581
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HRID 1708581 반응식
C1(N=C=NC2CCCCC2)CCCCC1.[CH3:16][N:17]1[C:25]2[C:20](=[CH:21][C:22]([N+:26]([O-:28])=[O:27])=[CH:23][CH:24]=2)[C:19]([CH2:29][C:30]2[CH:38]=[CH:37][C:33]([C:34]([OH:36])=[O:35])=[CH:32][C:31]=2[O:39][CH3:40])=[CH:18]1.[Cl:41][C:42]1[CH:47]=[C:46]([Cl:48])[C:45]([Cl:49])=[CH:44][C:43]=1O>CN(C)C1C=CN=CC=1.O1CCCC1>[Cl:41][C:42]1[CH:47]=[C:46]([Cl:48])[C:45]([Cl:49])=[CH:44][C:43]=1[O:35][C:34](=[O:36])[C:33]1[CH:37]=[CH:38][C:30]([CH2:29][C:19]2[C:20]3[C:25](=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=3)[N:17]([CH3:16])[CH:18]=2)=[C:31]([O:39][CH3:40])[CH:32]=1
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참가 물질

6

반응물 3

HCID 72712,4,5-TrichlorophenolHCID 10868DicyclohexylcarbodiimideHCID 11473264Benzoic acid, 3-methoxy-4-[(1-methyl-5-nitro-1H-indol-3-yl)methyl]-

생성물 1

HCID 67799125HCID 67799125, 화합물수율 67%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매
HCID 8028
Tetrahydrofuran
용매

실험 절차

1.66 g of dicyclohexylcarbodiimide are added at room temperature, with stirring and in a nitrogen atmosphere, to a mixture of 2.38 g of 4-(1-methyl-5-nitroindol-3-ylmethyl)-3-methoxybenzoic acid [Example 1, Process Step a1)], 1.48 g of 2,4,5-trichlorophenol and 1.0 g of 4-dimethylaminopyridine in 140 ml of tetrahydrofuran. The reaction mixture is stirred at room temperature for 15 hours and filtered. The filtrate is concentrated by evaporation in vacuo at 50° and the residue is dissolved in 400 ml of chloroform, with heating. The organic phase is washed at room temperature with 50 ml of 2N hydrochloric acid and 50 ml of water and dried over magnesium sulfate, and the solution is concentrated to dryness at 40° under 11 torr. The residue is chromatographed on 350 g of silica gel (eluant: dichloromethane). The 3-methoxy-4-(1-methyl-5-nitroindol-3-ylmethyl)-benzoic acid 2,4,5-trichlorophenyl ester obtained in that manner is suspended in 50 ml of ether and isolated by filtration. Yield 67%. Yellow crystals of m.p. 235°-236°.

후처리

  1. filtrationfiltered
  2. concentrationThe filtrate is concentrated by evaporation in vacuo at 50°
  3. dissolutionthe residue is dissolved in 400 ml of chloroform
  4. temperaturewith heating
  5. washThe organic phase is washed at room temperature with 50 ml of 2N hydrochloric acid and 50 ml of water
  6. dry with materialdried over magnesium sulfate
  7. concentrationthe solution is concentrated to dryness at 40° under 11 torr
  8. customThe residue is chromatographed on 350 g of silica gel (eluant: dichloromethane)

출처 및 근거

ORD 기록
ord-54c31f9753914d2ab4986dfebf5ee90b
출처 데이터셋
uspto-grants-1994_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05359083

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