Sodium Hydroxide → Dimethomorph

HRID 2396877

反応式

HRID 2396877 の反応式
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=2)=O)=[CH:4][CH:3]=1.[C:20]([N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)(=[O:22])[CH3:21].[OH-].[Na+]>CCCCCCCC>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=2)=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[O:22])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 155434-Acetylmorpholine2 回HCID 798751(4-Chlorophenyl)(3,4-dimethoxyphenyl)methanone

生成物 1

HCID 86298Dimethomorph

試薬・触媒・溶媒 1

HCID 356Octane溶媒

反応条件

温度
127 °C

実験手順

4-Chloro-3', 4'-dimethoxybenzophenone (276.7 g; 1 mol), N-acetyl morpholine (387.6 g; 3 mol) and powdered sodium hydroxide (40.0 g; 1 mol) in n-octane (600 ml) were refluxed under stirring for 10 hours at a column internal temperature of 127° C. The refluxing condensate (3 l/h) was passed through a column packed with molecular sieves (4 A, 150 g). Subsequently, n-octane (450 ml) was distilled off and toluene (1 l) was added. The mixture was heated to 80° C. and extracted once with 500 ml water and twice with 250 ml water. The organic layer was separated, and dried by azeotropic distillation of a part of the solvent (125 ml) under reduced pressure. On cooling to room temperature, crystallisation already started. Under continuous stirring, 750 ml petroleum ether (bp. 58°-63° C.) was added over a period of 30 minutes. After standing overnight, the crystals were collected by vacuum filtration washed with toluene/petroleum ether (1:3; 400 ml) and dried. Yield: 268 g (69.1%). Mp.: 140°-152° C. The product was 98.1% pure and contained 0.9% of the original ketone. The mother liquor contained an additional 25.2 g of the title compound and 42.2 g of the original ketone. The water washings contained 207 g =1.6 mol N-acetyl morpholine.

後処理

  1. distillationSubsequently, n-octane (450 ml) was distilled off
  2. additiontoluene (1 l) was added
  3. temperatureThe mixture was heated to 80° C.
  4. extractionextracted once with 500 ml water and twice with 250 ml water
  5. customThe organic layer was separated
  6. dry with materialdried by azeotropic distillation of a part of the solvent (125 ml) under reduced pressure
  7. temperatureOn cooling to room temperature
  8. customcrystallisation
  9. additionUnder continuous stirring, 750 ml petroleum ether (bp. 58°-63° C.) was added over a period of 30 minutes
  10. waitAfter standing overnight
  11. filtrationthe crystals were collected by vacuum filtration
  12. washwashed with toluene/petroleum ether (1:3; 400 ml)
  13. customdried

出典と根拠

ORDレコード
ord-55ad96dbdabd4daf87ac03a6fb2588a4
出典データセット
uspto-grants-1996_02
特許番号
US05495019

関連ノート

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