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Water → 3-(biphenyl-4-ylsulfonyl)-N-[cyano(phenyl)methyl]-1,3-thiazolidine-2-carboxamide

HRID 1964843
ノート
印刷プレビュー

反応式

HRID 1964843 の反応式
[NH2:1][C:2](=O)[CH:3]([NH:10][C:11]([CH:13]1[N:17]([S:18]([C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH2:16][CH2:15][S:14]1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.N1C(Cl)=NC(Cl)=NC=1Cl.O>CN(C=O)C>[C:24]1([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:25]=[CH:26][C:21]([S:18]([N:17]2[CH2:16][CH2:15][S:14][CH:13]2[C:11]([NH:10][CH:3]([C:2]#[N:1])[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:12])(=[O:19])=[O:20])=[CH:22][CH:23]=1
参加物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 962WaterHCID 7954Cyanuric chlorideHCID 10288863N-(2-amino-2-oxo-1-phenylethyl)-3-(biphenyl-4-ylsulfonyl)-1,3-thiazolidine-2-carboxamide

生成物 1

HCID 101739433-(biphenyl-4-ylsulfonyl)-N-[cyano(phenyl)methyl]-1,3-thiazolidine-2-carboxamide収率 69.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of compound 1b, e.g., N-(2-amino-2-oxo-1-phenylethyl)-3-(biphenyl-4-ylsulfonyl)-1,3-thiazolidine-2-carboxamide (385 mg, 0.8 mmol) in DMF (1 mL) at RT was added cyanuric chloride (74 mg, 0.4 mmol) in one portion. After one night, the reaction was done. Water (3 mL) was added and a precipitate was formed. The aqueous phase was extracted with two portions of EtOAc (5 mL). Combined organic phases were washed with 5% aqueous sodium bicarbonate, with water, dried over MgSO4 and concentrated under reduced pressure. A light yellow solid was isolated and was purified by flash chromatography (Cyclohexane/EtOAc gradient form 8:2 to 1:1), affording product Ic, e.g., 3-(biphenyl-4-ylsulfonyl)-N-[cyano(phenyl)methyl]-1,3-thiazolidine-2-carboxamide (257 mg, 69% yield) in 100% purity by HPLC.

後処理

  1. waitAfter one night
  2. customa precipitate was formed
  3. extractionThe aqueous phase was extracted with two portions of EtOAc (5 mL)
  4. washCombined organic phases were washed with 5% aqueous sodium bicarbonate, with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customA light yellow solid was isolated
  8. customwas purified by flash chromatography (Cyclohexane/EtOAc gradient form 8:2 to 1:1)

出典と根拠

ORDレコード
ord-330b252f48f9441fb1eaaa0019bf2c26
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08415480B2

反応ノート

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