Imidazole → N-(4-cyano-2-t-butyldimethylsilanoxyphenyl)-N'-(2-bromophenyl)thio urea

HRID 413342노트

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HRID 413342 반응식
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Br:19])=[S:11])=[C:5]([OH:20])[CH:4]=1)#[N:2].N1C=CN=C1.[CH3:26][C:27]([Si:30](Cl)([CH3:32])[CH3:31])([CH3:29])[CH3:28]>C1COCC1>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Br:19])=[S:11])=[C:5]([O:20][Si:30]([C:27]([CH3:29])([CH3:28])[CH3:26])([CH3:32])[CH3:31])[CH:4]=1)#[N:2]

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 12043084N-(4-cyano-2-hydroxyphenyl)-N'-(2-bromophenyl) thiourea

생성물 1

HCID 12043082N-(4-cyano-2-t-butyldimethylsilanoxyphenyl)-N'-(2-bromophenyl)thio urea수율 84.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of N-(4-cyano-2-hydroxyphenyl)-N′-(2-bromophenyl)thio urea (3.5 g, 10 mmol) in THF (50 mL) at 0° C. was added imidazole (1.0 g, 15 mmol) and TBSCl (1.5 g, 10 mmol). After 1 h, the reaction mixture quenched with water (100 mL) and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude material was crystallized from ethyl acetate to give 3.9 g (84%) of N-(4-cyano-2-t-butyldimethylsilanoxyphenyl)-N′-(2-bromophenyl)thio urea as a yellow solid. 1H NMR (400 MHz, DMSO) δ 9.9 (s, 1H), 9.2 (s, 1H), 8.1 (d, 1H), 7.7 (d, 1H), 7.6 (d, 1H), 7.45 (d, 1H), 7.4 (t, 1H), 7.35 (s, 1H), 7.2 (t, 1H); MS(EI) m/e 347 (100 (M+)), 175 (40), 461 (40).

후처리

  1. customthe reaction mixture quenched with water (100 mL)
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was crystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-a4da80806b9241498622a317474c76bd
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06566387B1

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