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3-(Trifluoromethyl)benzoyl chloride → HCID 20085643, 화합물

HRID 1608814
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HRID 1608814 반응식
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21]([NH:24][CH2:25][CH2:26][CH2:27][N:28]1[CH:32]=[CH:31][N:30]=[CH:29]1)(=[O:23])=[O:22]>ClCCl.N1C=CC=CC=1.C(OCC)(=O)C>[N:28]1([CH2:27][CH2:26][CH2:25][NH:24][S:21]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[NH:14][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][CH:11]=[C:3]([C:2]([F:13])([F:12])[F:1])[CH:4]=2)(=[O:23])=[O:22])[CH:32]=[CH:31][N:30]=[CH:29]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 2

HCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 15225171HCID 15225171, 화합물

생성물 1

HCID 20085643HCID 20085643, 화합물수율 58.9%

시약·촉매·용매 3

HCID 1049Pyridine용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 4.24 g (0.0203 mol) of m-trifluoromethylbenzoyl chloride in 10 ml of dichloromethane was added dropwise to a solution of 4.35 g (0.0153 mol) of 2-amino-N-[(3-imidazol-1-yl)propyl]benzenesulfonamide, prepared as in Examples 1A and 1B, in 70 ml of pyridine, under nitrogen. When the reaction was complete, as determined by thin layer chromatography, the resulting reaction mixture was reduced to dryness under reduced pressure. The resultant oil was dissolved in an ethyl acetate/aqueous sodium bicarbonate mixture. The resulting layers were separated, the organic layer was washed with water and again reduced to dryness under reduced pressure to provide an oil. This oil was then purified using column chromatography (8000 ml of a gradient eluent of 0-15% methanol in chloroform). The fractions containing the desired product were combined, reduced to dryness under reduced pressure and then recrystallized from an ethanol/hexane/diethyl ether solution to provide 4.08 g of the desired titled compound (m.p. 145°-147° C.).

후처리

  1. customthe resulting reaction mixture
  2. customThe resulting layers were separated
  3. washthe organic layer was washed with water
  4. customto provide an oil
  5. customThis oil was then purified
  6. additionThe fractions containing the desired product
  7. customrecrystallized from an ethanol/hexane/diethyl ether solution

출처 및 근거

ORD 기록
ord-f48e3c794d964a71b20704a2248ee5f5
출처 데이터셋
uspto-grants-1995_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05397798

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