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

HRID 1428740ノート

反応式

HRID 1428740 の反応式
[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]([F: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>[F: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]

参加物

7

反応物 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 86679367N-(4-amino-2-fluorobenzyl)methanesulfonamide

生成物 1

HCID 86679368Phenyl 3-fluoro-4-(methylsulfonamidomethyl)phenylcarbamate収率 85%

試薬・触媒・溶媒 3

HCID 6342Acetonitrile溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of N-(4-amino-2-fluorobenzyl)methanesulfonamide (190 mg, 0.871 mmol) in tetrahydrofuran and acetonitrile as co-solvent were added phenylchloroformate (0.115 ml, 0.914 mmol) and pyridine (0.084 ml, 1.045 mmol). The reaction mixture was stirred for 1 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 was removed in vacuo. The crude was purified by column chromatography. Phenyl 3-fluoro-4-(methylsulfonamidomethyl)phenylcarbamate (250 mg) was obtained as 85% yield.

後処理

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

出典と根拠

ORDレコード
ord-ecfd50b90de44a79ae2b49c635cca9b9
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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