Aniline → 2-(N-tert-butylsulfamoyl)-N-phenylacetamide

HRID 553466노트

반응식

HRID 553466 반응식
[C:1]([NH:5][S:6]([CH2:9][C:10]([OH:12])=O)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:13]1[CH:14]=[CH:15][C:16]2N(O)N=[N:19][C:17]=2[CH:18]=1.CCN=C=NCCCN(C)C.NC1C=CC=CC=1>C1COCC1>[C:1]([NH:5][S:6]([CH2:9][C:10]([NH:19][C:17]1[CH:18]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:12])(=[O:7])=[O:8])([CH3:2])([CH3:3])[CH3:4]

참가 물질

6

반응물 4

HCID 6115AnilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 287734162-(Tert-butylsulfamoyl)acetic acid

생성물 1

HCID 579245132-(N-tert-butylsulfamoyl)-N-phenylacetamide수율 51%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of compound 2-(N-tert-butylsulfamoyl)acetic acid (5 g, 25.6 mmol.) in dry THF (20 mL) was added HOBt (13.8 g, 102.4 mmol.) and EDCI (18.3 g, 102.4 mmol.). Then aniline (3.6 g, 38.4 mmol.) was added successively. The reaction mixture was stirred overnight at room temperature. TLC analysis showed the reaction complete. The mixture was quenched by adding water and extracted with EtOAc (30 mL×3). The combined organic layer was dried over Na2SO4, concentrated. The residue was purified by column chromatography (PE:EtOAc=2:1) to afford 2-(N-tert-butylsulfamoyl)-N-phenylacetamide (3.5 g, 51%).

후처리

  1. customThe mixture was quenched
  2. additionby adding water
  3. extractionextracted with EtOAc (30 mL×3)
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (PE:EtOAc=2:1)

출처 및 근거

ORD 기록
ord-892091d29f62465280eb95453981985f
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08048862B2

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