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Thiophosgene → N-(2-tert-butyldimethysilyloxy-4-nitrophenyl)-N'-phenyl-thiourea

HRID 612629
ノート
印刷プレビュー

反応式

HRID 612629 の反応式
[Si:1]([O:8][C:9]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:10]=1[NH2:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([O-])(O)=O.[Na+].[C:24](Cl)(Cl)=[S:25]>C(Cl)(Cl)Cl.O>[Si:1]([O:8][C:9]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:10]=1[NH:11][C:24]([NH:11][C:10]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:9]=1)=[S:25])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 10040ThiophosgeneHCID 516892Sodium BicarbonateHCID 154857102-[(Tert-butyldimethylsilyl)oxy]-4-nitroaniline

生成物 1

HCID 15524278N-(2-tert-butyldimethysilyloxy-4-nitrophenyl)-N'-phenyl-thiourea収率 98%

試薬・触媒・溶媒 1

HCID 22418719Chloroform water溶媒

反応条件

温度
23 °C

実験手順

N-(2-tert-Butyldimethysilyloxy-4-nitrophenyl)-N'-phenyl-thiourea was prepared by treating a biphasic solution of 2-tert-butyldimethysilyloxy-4-nitroaniline (80 mg, 0.308 mmol) and NaHCO3 in CHCl3 :H2O (2.5:1, 7 mL) with thiophosgene at 0° C. The solution was allowed to warm to 23° C. and the reaction was continued overnight. The CHCl3 layer was separated and dried over sodium sulfate. The solution was concentrated in vacuo and the residue was dissolved in toluene and treated with aniline (100 uL) at 23° C. for 12 h. The reaction mixture was concentrated and the residue was purified by flash chromatography (10% EtOAc/hexanes) to afford the titled compound as a yellow solid (120.8 mg, 98%) mp: 144-145° C.; 1H NMR (CD3OD/CDCl3): δ 8.65 (d, 1H, J=10.0 Hz), 7.58 d, 1H, J=10.0 Hz), 7.47 (d, 1H, J=1.25 Hz), 7.26 (m, 4H), 7.10 (m, 1H).

後処理

  1. customN-(2-tert-Butyldimethysilyloxy-4-nitrophenyl)-N'-phenyl-thiourea was prepared
  2. customThe CHCl3 layer was separated
  3. dry with materialdried over sodium sulfate
  4. concentrationThe solution was concentrated in vacuo
  5. dissolutionthe residue was dissolved in toluene
  6. additiontreated with aniline (100 uL) at 23° C. for 12 h
  7. concentrationThe reaction mixture was concentrated
  8. customthe residue was purified by flash chromatography (10% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-0780d738d55147469d44e8e39198913e
出典データセット
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06005008

反応ノート

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