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Sulfuric Acid → N-[2-chloro-1-[4'-[(difluoromethyl)thio][1,1'-biphenyl]-4-yl]ethyl]-2,6-difluorobenzamide

HRID 1108159
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인쇄 미리보기

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HRID 1108159 반응식
[Cl:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([S:17][CH:18]([F:20])[F:19])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)O.[F:21][C:22]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:23]=1[C:24]#[N:25].S(=O)(=O)(O)[OH:32]>ClCCl>[Cl:1][CH2:2][CH:3]([NH:25][C:24](=[O:32])[C:23]1[C:22]([F:21])=[CH:29][CH:28]=[CH:27][C:26]=1[F:30])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([S:17][CH:18]([F:20])[F:19])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1
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참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 746952,6-DifluorobenzonitrileHCID 18786418alpha-(Chloromethyl)-4'-[(difluoromethyl)thio][1,1'-biphenyl]-4-methanol

생성물 1

HCID 18786412N-[2-chloro-1-[4'-[(difluoromethyl)thio][1,1'-biphenyl]-4-yl]ethyl]-2,6-difluorobenzamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
5 °C

실험 절차

A mixture of 2.0 g of α-(chloromethyl)-4'-[(difluoromethyl)thio][1,1'-biphenyl]-4-methanol, 4.0 g of 2,6-difluorobenzonitrile, and 15 mL of dichloromethane was cooled to 5° C. and 0.8 mL of conc. sulfuric acid was added dropwise over 7 min. After 30 min, ice was added, the mixture was diluted with hexanes, and the crude product was filtered and dried to afford 1.0 g of product, m.p. 144-145° C. 1H-NMR (CDCl3): δ4.0 (dq, 2), 5.6 (m, 1H), 6.75 (br d, 1H), 6.85 (t, 1H, J=60 Hz), 7.0 (t, 2H), 7.4 (m, 1H), 7.5 (d, 2H), 7.6 (m, 6H). The filtrate was extracted with ethyl acetate; the extract was washed with water, concentrated, and chromatographed on silica gel to afford an additional 0.5 g of product, corresponding to a total yield of 52%.

후처리

  1. additionice was added
  2. filtrationthe crude product was filtered
  3. customdried

출처 및 근거

ORD 기록
ord-49c934ab843c4ee99893b14191cce85d
출처 데이터셋
uspto-grants-2000_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06063932

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