Pyridine → Phenyl 3-methyl-4-(methylsulfonamidomethyl)phenylcarbamate

HRID 1428762노트

반응식

HRID 1428762 반응식
[NH2:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][NH:7][S:8]([CH3:11])(=[O:10])=[O:9])=[C:4]([CH3:14])[CH:3]=1.[C:15]1([O:21][C:22](Cl)=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.N1C=CC=CC=1>O1CCCC1.C(#N)C.C(OCC)(=O)C>[CH3:14][C:4]1[CH:3]=[C:2]([NH:1][C:22](=[O:23])[O:21][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:12][C:5]=1[CH2:6][NH:7][S:8]([CH3:11])(=[O:10])=[O:9]

참가 물질

7

반응물 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 86679390N-(4-amino-2-methylbenzyl)methanesulfonamide

생성물 1

HCID 86679391Phenyl 3-methyl-4-(methylsulfonamidomethyl)phenylcarbamate수율 98%

시약·촉매·용매 3

HCID 6342Acetonitrile용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of N-(4-amino-2-methylbenzyl)methanesulfonamide (61 mg, 0.285 mmol) in tetrahydrofuran and acetonitrile as co-solvent were added phenylchloroformate (0.04 mL, 0.299 mmol) and pyridine (0.03 mL, 0.342 mmol). The reaction mixture was stirred for 3 h at room temperature. The mixture dissolved in ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography to give phenyl 3-methyl-4-(methylsulfonamidomethyl)phenylcarbamate (93 mg, 98%).

후처리

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customThe filtrate removed in vacuo
  5. customThe crude was purified by column chromatography

출처 및 근거

ORD 기록
ord-e8c6499335e44458b981a09d07550392
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08937092B2

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