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Chloromethyl Methyl Ether → (NE)-3-chloro-4-fluoro-N-[1-(methoxymethyl)pyrimidin-4-ylidene]benzenesulfonamide

HRID 1402030
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HRID 1402030 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([NH:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][N:14]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8].C(N(CC)C(C)C)(C)C.[CH3:28][O:29][CH2:30]Cl>C(Cl)Cl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([S:9](/[N:12]=[C:13]2/[N:14]=[CH:15][N:16]([CH2:28][O:29][CH3:30])[CH:17]=[CH:18]/2)(=[O:10])=[O:11])[CH:5]=[CH:6][C:7]=1[F:8]
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참가 물질

6

반응물 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 594364913-chloro-4-fluoro-N-pyrimidin-4-ylbenzenesulfonamide

생성물 1

HCID 59436500(NE)-3-chloro-4-fluoro-N-[1-(methoxymethyl)pyrimidin-4-ylidene]benzenesulfonamide수율 91.6%

시약·촉매·용매 2

HCID 6344Dichloromethane용매
HCID 8857
Ethyl Acetate
용매

실험 절차

To 3-chloro-4-fluoro-N-pyrimidin-4-ylbenzenesulfonamide (Preparation 426, 73 mg, 0.25 mmol) in methylene chloride (2 mL) cooled at 0° C. was added N,N-diisopropylethylamine (0.066 mL, 0.38 mmol) and chloromethyl methyl ether (0.025 mL, 0.28 mmol). After stirring at room temperature for 18 hours, the reaction mixture was diluted with ethyl acetate, washed successively with 1N aqueous sodium hydroxide, water, saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated to give 76 mg (90%) of the title compound as an orange oil and a mixture of three regioisomers that were not separated.

후처리

  1. washwashed successively with 1N aqueous sodium hydroxide, water, saturated aqueous sodium chloride solution
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3b44a217b2f94f97b65b7904ed9cabec
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08907101B2

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