Pyridine → 2,3-Difluorophenyl(phenyl)carbamic Chloride

HRID 341360ノート

反応式

HRID 341360 の反応式
[F:1][C:2]1[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:3]=1[NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Cl:16][C:17](Cl)([O:19]C(=O)OC(Cl)(Cl)Cl)Cl.N1C=CC=CC=1>C(Cl)Cl>[F:1][C:2]1[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:3]=1[N:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:17]([Cl:16])=[O:19]

参加物

5

反応物 3

HCID 1049PyridineHCID 94429TriphosgeneHCID 669111232,3-difluoro-N-phenylaniline

生成物 1

HCID 866516992,3-Difluorophenyl(phenyl)carbamic Chloride収率 88%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2,3-Difluoro-N-phenylaniline (100 mg, 0.487 mmol) and triphosgene (159 mg, 0.536 mmol) were dissolved in CH2Cl2 (1 mL). The solution was cooled in an ice bath, and pyridine (79 μL, 0.975 mmol) was added slowly. Upon complete addition, the reaction was warmed to room temperature and stirred for 1 h. Then, it was cooled in an ice bath and quenched by the slow addition of H2O (1 mL). The reaction mixture was extracted with H2O (5 mL) and CH2Cl2 (5 mL). The aqueous layer was extracted again with CH2Cl2 (5 mL). The organic layers were combined and washed once with H2O (10 mL), dried over MgSO4, and concentrated. The residue was purified by silica gel column chromatography to yield the title compound as a light brown oil (114.7 mg).

後処理

  1. temperatureThe solution was cooled in an ice bath
  2. additionUpon complete addition
  3. temperatureThen, it was cooled in an ice bath
  4. customquenched by the slow addition of H2O (1 mL)
  5. extractionThe reaction mixture was extracted with H2O (5 mL) and CH2Cl2 (5 mL)
  6. extractionThe aqueous layer was extracted again with CH2Cl2 (5 mL)
  7. washwashed once with H2O (10 mL)
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-fdb261b4822d4e19b0b6e5b8df5487b5
出典データセット
uspto-grants-2014_11
特許番号
US08895776B2

反応ノート

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