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Sulfuric Acid → 5-(3,5-Dichlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-ylmethyl acetylcarbamate

HRID 1005545
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HRID 1005545 반응식
[OH:1][CH2:2][C:3]1[N:4]([CH2:20][CH3:21])[C:5]([S:11][C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[C:14]([Cl:19])[CH:13]=2)=[C:6]([CH:8]([CH3:10])[CH3:9])[N:7]=1.S(=O)(=O)(O)[OH:23].C([N:29]([CH2:32]C)CC)C.C(O[C:38](=[O:40])[CH3:39])(=O)C>>[C:38]([NH:29][C:32](=[O:23])[O:1][CH2:2][C:3]1[N:4]([CH2:20][CH3:21])[C:5]([S:11][C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[C:14]([Cl:19])[CH:13]=2)=[C:6]([CH:8]([CH3:9])[CH3:10])[N:7]=1)(=[O:40])[CH3:39]
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참가 물질

5

반응물 4

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 473933(5-(3,5-Dichlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-yl)methanol

생성물 1

HCID 4781885-(3,5-Dichlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-ylmethyl acetylcarbamate수율 35%

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온도
110 °C

실험 절차

To a suspension of the compound 19 (77.6 mg, 0.200 mmol) in acetic anhydride (1 mL) was added conc. sulfuric acid (0.24 eq.), and heated with reflux at 110° C. for 1 hour. Triethylamine (0.1 mL) was added to the reaction mixture, and the mixture was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column (eluate: ethyl acetate) to give the compound 80 (31 mg, 35%) as crystals. Mp. 163-164° C. (hexane-ether) Rf 0.10 (1:2 EtOAc - hexane)

후처리

  1. temperatureheated
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customThe residue was purified by chromatography on a silica gel column (eluate: ethyl acetate)

출처 및 근거

ORD 기록
ord-3fc16d5043d84235b8b744692a71e038
출처 데이터셋
uspto-grants-2000_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06054591

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