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Triethylamine → N-(4-cyano-2-t-butyldimethylsilanoxyphenyl)-N'-(2-bromophenyl)carbodiimide

HRID 413343
ノート
印刷プレビュー

反応式

HRID 413343 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)=[C:5]([O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH:4]=1)#[N:2].C(N(CC)CC)C.CS(Cl)(=O)=O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]=[C:10]=[N:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Br:19])=[C:5]([O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:22])[CH3:23])[CH:4]=1)#[N:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 12043082N-(4-cyano-2-t-butyldimethylsilanoxyphenyl)-N'-(2-bromophenyl)thio urea

生成物 1

HCID 12043083N-(4-cyano-2-t-butyldimethylsilanoxyphenyl)-N'-(2-bromophenyl)carbodiimide収率 104.1%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒
HCID 6344
Dichloromethane
溶媒

実験手順

To a solution of N-(4-cyano-2-t-butyldimethylsilanoxyphenyl)-N′-(2-bromophenyl)thio urea (3.4 g, 7.4 mmol) in methylene chloride (40 mL) at 0° C. was added triethylamine (3.1 mL, 22 mmol), DMAP (20 mg) and methane sulfonyl chloride (1.1 mL, 15 mmol). After 25 min, the reaction mixture was 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 to give 3.3 g (100%) of N-(4-cyano-2-t-butyldimethylsilanoxyphenyl)-N′-(2-bromophenyl)carbodiimide as a yellow solid which required no further purification. 1H NMR (400 MHz, DMSO) δ 7.7 (d, 1H), 7.45 (d, 1H), 7.4 (m, 4H), 7.15 (t, 1H).

後処理

  1. customthe reaction mixture was 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

出典と根拠

ORDレコード
ord-e53b2ec8d81d4a98b6f257b0907e0246
出典データセット
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06566387B1

反応ノート

読み込み中…

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