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1,5-Dichloro-2-isothiocyanato-3-methylbenzene → Methyl 4-chloro-3-{[(2,4-dichloro-6-methylphenyl)carbamothioyl]amino}-2-[(3-hydroxypropyl)amino]benzoate

HRID 1628486
ノート
印刷プレビュー

反応式

HRID 1628486 の反応式
[NH2:1][C:2]1[C:3]([NH:13][CH2:14][CH2:15][CH2:16][OH:17])=[C:4]([CH:9]=[CH:10][C:11]=1[Cl:12])[C:5]([O:7][CH3:8])=[O:6].[Cl:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([CH3:26])[C:20]=1[N:27]=[C:28]=[S:29]>O1CCCC1.C(=O)([O-])O.[Na+]>[Cl:12][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[C:3]([NH:13][CH2:14][CH2:15][CH2:16][OH:17])[C:2]=1[NH:1][C:28](=[S:29])[NH:27][C:20]1[C:21]([CH3:26])=[CH:22][C:23]([Cl:25])=[CH:24][C:19]=1[Cl:18]
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 2

HCID 27360131,5-Dichloro-2-isothiocyanato-3-methylbenzeneHCID 68739849Methyl 3-amino-4-chloro-2-((3-hydroxypropyl)amino]benzoate

生成物 1

HCID 86632880Methyl 4-chloro-3-{[(2,4-dichloro-6-methylphenyl)carbamothioyl]amino}-2-[(3-hydroxypropyl)amino]benzoate収率 79%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 516892
Sodium Bicarbonate
溶媒

反応条件

温度
60 °C

実験手順

A mixture of methyl 3-amino-4-chloro-2-[(3-hydroxypropyl)amino]benzoate (1.50 g, 5.80 mmol) and 1,5-dichloro-2-isothiocyanato-3-methylbenzene (1.64 g, 7.52 mmol) in tetrahydrofuran (15 mL) was stirred at 60° C. for 17 hr. The mixture was diluted with saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was washed with diisopropyl ether to give the title compound as a brown powder (2.18 g, 4.57 mmol, 79%).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washThe residue was washed with diisopropyl ether

出典と根拠

ORDレコード
ord-db779d3b7e2d454ba5c628bf25576df8
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08785460B2

反応ノート

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