2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 2-(2,4-Dichlorophenyl)-5-methoxybenzoxazole

HRID 1245364

反応式

HRID 1245364 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[OH:10].[Cl:11][C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[CH:19]=O.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>CO.ClCCl>[Cl:11][C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[C:19]1[O:10][C:3]2[CH:4]=[CH:5][C:6]([O:8][CH3:9])=[CH:7][C:2]=2[N:1]=1

参加物

6

反応物 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 134042,4-DichlorobenzaldehydeHCID 14191082-Amino-4-methoxyphenol

生成物 1

HCID 219116842-(2,4-Dichlorophenyl)-5-methoxybenzoxazole

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
45 °C

実験手順

To a solution of 2-amino-4-methoxyphenol (1 g, 7.1 mmol), a compound of formula (j) in 20 mL MeOH was added (2,4-dichlorophenyl)formaldehyde (1.2 g, 7.1 mmol), a compound of formula (k). The mixture was heated at 45° C. for 12 hours. The mixture was concentrated under reduced pressure and the residue was dissolved in 50 mL dichloromethane. To the solution was added DDQ (1.7 g, 7.8 mmol), and the mixture was allowed to stir at room temperature for 30 minutes. The reaction mixture was then diluted with an additional 30 mL of dichloromethane and washed sequentially with saturated NaHCO3 (2×50 mL) and brine. The organic layer was separated, dried over MgSO4 and concentrated under reduced pressure to yield 2-(2,4-dichlorophenyl)-5-methoxybenzoxazole, a compound of formula (1), which was purified using flash column chromatography.

後処理

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in 50 mL dichloromethane
  3. washwashed sequentially with saturated NaHCO3 (2×50 mL) and brine
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-3580df681d8242cf8b3e4abb1f0a8665
出典データセット
uspto-grants-2006_10
特許番号
US07125876B2

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