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Dimethylformamide → 3-Phenyl-2-[4-[3-(1-pyrrolidinyl)propoxy]phenyl]-1,4-benzoxathiin

HRID 1696685
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인쇄 미리보기

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HRID 1696685 반응식
C(=O)([O-])[O-].[K+].[K+].Br.BrC[CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.CN(C=O)C.[C:23]1([C:29]2[S:34][C:33]3[CH:35]=[CH:36][CH:37]=[CH:38][C:32]=3[O:31][C:30]=2[C:39]2[CH:44]=[CH:43][C:42]([OH:45])=[CH:41][CH:40]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(OCC)(=O)C>[C:23]1([C:29]2[S:34][C:33]3[CH:35]=[CH:36][CH:37]=[CH:38][C:32]=3[O:31][C:30]=2[C:39]2[CH:40]=[CH:41][C:42]([O:45][CH2:15][CH2:16][CH2:17][N:12]3[CH2:11][CH2:10][CH2:14][CH2:13]3)=[CH:43][CH:44]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 201357721-(3-Bromopropyl)piperidine HydrobromideHCID 593967364-(3-Phenyl-1,4-benzoxathiin-2-yl)phenol

생성물 1

HCID 593967663-Phenyl-2-[4-[3-(1-pyrrolidinyl)propoxy]phenyl]-1,4-benzoxathiin수율 53.5%

시약·촉매·용매 1

HCID 8857
Ethyl Acetate
용매

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온도
80 °C

실험 절차

Potassium carbonate (83 mg) and 1-(3-bromopropyl)piperidine hydrobromide (54.6 mg) were added to a DMF (3 mL) solution of 4-(3-phenyl-1,4-benzoxathiin-2-yl)phenol (63.7 mg, 0.2 mmol) obtained in Reference Example 1-1, and stirred at 80° C. for 8 hours. The reaction liquid was restored to room temperature, diluted with ethyl acetate, and extracted with distilled water. The organic layer was dried with magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by preparative thin-layer silica gel column chromatography (chloroform:methanol=9:1) to obtain the entitled compound (43.7 mg, 51%) as a yellow oil.

후처리

  1. customobtained in Reference Example 1-1
  2. customThe reaction liquid
  3. customwas restored to room temperature
  4. extractionextracted with distilled water
  5. dry with materialThe organic layer was dried with magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by preparative thin-layer silica gel column chromatography (chloroform:methanol=9:1)

출처 및 근거

ORD 기록
ord-faf5a1f3c14d4aeaabe3000da1f38c21
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08163770B2

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