Pyridine → Phenyl 4-(ethylsulfonamidomethyl)phenylcarbamate

HRID 1428767ノート

反応式

HRID 1428767 の反応式
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][NH:7][S:8]([CH2:11][CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:22]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:23]>C(#N)C.O1CCCC1>[CH2:11]([S:8]([NH:7][CH2:6][C:5]1[CH:13]=[CH:14][C:2]([NH:1][C:22](=[O:23])[O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:3][CH:4]=1)(=[O:10])=[O:9])[CH3:12]

参加物

6

反応物 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 39243426N-(4-aminobenzyl)ethanesulfonamide

生成物 1

HCID 86680222Phenyl 4-(ethylsulfonamidomethyl)phenylcarbamate収率 88.7%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

N-(4-Aminobenzyl)ethanesulfonamide (504 mg, 2.35 mmol) was dissolved in acetonitrile (3 mL) and tetrahydrofuran (4 mL). The reaction mixture was added pyridine (0.23 mL, 2.78 mmol) and phenyl chloroformate (0.31 mL, 2.43 mmol) and stirred at room temperature for 3 h under nitrogen atmosphere. TLC showed complete consumption of starting material. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic part was washed with water and brine. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The crude was purified by column chromatography to give phenyl 4-(ethylsulfonamidomethyl)phenylcarbamate (697 mg, 87%).

後処理

  1. customconsumption of starting material
  2. additionThe reaction mixture was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe organic part was washed with water and brine
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude was purified by column chromatography

出典と根拠

ORDレコード
ord-acd089da99c04ca696f32be790e2eb73
出典データセット
uspto-grants-2015_01
特許番号
US08937092B2

反応ノート

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