Thionyl Chloride → 2-(2,4-Dichloro-6-methoxyphenyl)-4,4-dimethyl-2-oxazoline

HRID 1285607

反応式

HRID 1285607 の反応式
O[CH2:2][C:3]([NH:6][C:7](=[O:18])[C:8]1[C:13]([O:14][CH3:15])=[CH:12][C:11]([Cl:16])=[CH:10][C:9]=1[Cl:17])([CH3:5])[CH3:4].S(Cl)(Cl)=O>CCOCC>[Cl:17][C:9]1[CH:10]=[C:11]([Cl:16])[CH:12]=[C:13]([O:14][CH3:15])[C:8]=1[C:7]1[O:18][CH2:2][C:3]([CH3:4])([CH3:5])[N:6]=1

参加物

4

反応物 2

HCID 24386Thionyl ChlorideHCID 128028822,4-dichloro-N-(1-hydroxy-2-methylpropan-2-yl)-6-methoxybenzamide

生成物 1

HCID 128028832-(2,4-Dichloro-6-methoxyphenyl)-4,4-dimethyl-2-oxazoline収率 70%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
20 °C

実験手順

N-(2-Hydroxy-1,1-dimethylethyl)-2,4-dichloro-6-methoxybenzamide (5.5 g, 18.8 mmol) was treated dropwise with thionyl chloride (5.5 ml) and stirred magnetically at 20° C. for 30 min. Dry ether (100 ml) was added, the mixture was stirred for an additional one hour and the oxazoline hydrochloride precipitate was collected by filtration. The salt was neutralized with 20% sodium hydroxide to afford an alkaline mixture which was extracted with ether. The ethereal extract was dried (MgSO4) and concentrated to give an oil (3.6 g, 70%), which crystallized on standing, mp 47°-50° C.

後処理

  1. stirringthe mixture was stirred for an additional one hour
  2. filtrationthe oxazoline hydrochloride precipitate was collected by filtration
  3. customto afford an alkaline mixture which
  4. extractionwas extracted with ether
  5. extractionThe ethereal extract
  6. dry with materialwas dried (MgSO4)
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-a96dc604fb3f41d39140d97f7fc8443a
出典データセット
uspto-grants-1986_01
特許番号
US04567289

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