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

HRID 413342ノート

反応式

HRID 413342 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a4da80806b9241498622a317474c76bd
出典データセット
uspto-grants-2003_05
特許番号
US06566387B1

反応ノート

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