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N-{3-[(2,5-Dichloropyrimidin-4-yl)amino]phenyl}-1-(3-nitrophenyl)methanesulfonamide → 1-(3-Aminophenyl)-N-{3-[(2,5-dichloropyrimidin-4-yl)amino]phenyl}methanesulfonamide

HRID 541830
ノート
印刷プレビュー

反応式

HRID 541830 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[C:11]([NH:15][S:16]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-])=O)[CH:21]=3)(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=2)[C:5]([Cl:29])=[CH:4][N:3]=1>O.CO.C(O)(=O)C.[Fe]>[NH2:26][C:22]1[CH:21]=[C:20]([CH2:19][S:16]([NH:15][C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([NH:8][C:6]3[C:5]([Cl:29])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=3)[CH:10]=2)(=[O:17])=[O:18])[CH:25]=[CH:24][CH:23]=1
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

6

反応物 1

HCID 86636268N-{3-[(2,5-Dichloropyrimidin-4-yl)amino]phenyl}-1-(3-nitrophenyl)methanesulfonamide

生成物 1

HCID 579618841-(3-Aminophenyl)-N-{3-[(2,5-dichloropyrimidin-4-yl)amino]phenyl}methanesulfonamide

試薬・触媒・溶媒 4

HCID 23925Iron触媒HCID 176Acetic Acid溶媒HCID 887Methanol溶媒
HCID 962
Water
溶媒

反応条件

温度
0 °C

実験手順

To a solution of N-{3-[(2,5-dichloropyrimidin-4-yl)amino]phenyl}-1-(3-nitrophenyl)methanesulfonamide (0.060 g, 0.13 mmol) in water (0.1 mL), methanol (0.5 mL) and acetic acid (0.20 mL) was added iron (0.030 g, 0.53 mmol) powder in one batch. The mixture was stirred at 0° C. for 0.5 h. The reaction was mixed with celite, filtered, and the cake was washed with EtOAc. The brown filtrate was concentrated and EtOAc and NaHCO3/water added. Water phase was extracted with EtOAc twice. The organics were combined, dried over Na2SO4 and concentrated to give the desired product as a yellow powder (0.050 g, 89%. LCMS for C17H15Cl2N5O2S (M+H)+: m/z=423.9, 426.0.

後処理

  1. additionThe reaction was mixed with celite
  2. filtrationfiltered
  3. washthe cake was washed with EtOAc
  4. concentrationThe brown filtrate was concentrated
  5. additionEtOAc and NaHCO3/water added
  6. extractionWater phase was extracted with EtOAc twice
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-be994e1bf78f4e3ca20b4602eb0b597f
出典データセット
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08871753B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート