Sodium hydride → 5-[4-(6-Chloro-2-pyridinyloxy)-phenoxymethyl]-2-ethoxy-1,3,4-thiadiazole

HRID 36622ノート

反応式

HRID 36622 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[H][H].Cl[CH2:21][C:22]1[S:26][C:25]([O:27][CH2:28][CH3:29])=[N:24][N:23]=1>CN(C)C=O>[Cl:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:21][C:22]3[S:26][C:25]([O:27][CH2:28][CH3:29])=[N:24][N:23]=3)=[CH:11][CH:10]=2)[CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 146736064-(6-Chloro-2-pyridinyloxy)phenolHCID 199376072-(Chloromethyl)-5-ethoxy-1,3,4-thiadiazoleHCID 178418361HCID 178418361、化合物

生成物 1

HCID 146736295-[4-(6-Chloro-2-pyridinyloxy)-phenoxymethyl]-2-ethoxy-1,3,4-thiadiazole収率 67.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

反応条件

温度
50 °C

実験手順

At room temperature (about 20° C.), 4.9 g of 4(6-chloro-2-pyridinyloxy)phenol in 40 ml of anhydrous dimethylformamide is dripped into 0.6 g of 100% strength sodium hydride in 20 ml of anhydrous dimethylformamide. To complete the exothermic reaction (evolution of hydrogen) the mixture is stirred for 30 minutes at 50° C. Subsequently, 4 g of 5-chloromethyl-2-ethoxy-1,3,4-thiadiazole in 20 ml of anhydrous dimethylformamide is dripped in and the mixture is stirred for 2 hours at 60° C. and overnight at room temperature. The mixture is then poured into 200 ml of ice water. The crude product which crystallizes out is filtered off and recrystallized from isopropanol. There is obtained 5.4 g of 5-[4-(6-chloro-2-pyridinyloxy)-phenoxymethyl]-2-ethoxy-1,3,4-thiadiazole of m.p.: 92° C.-94° C.

後処理

  1. customAt room temperature
  2. stirringis stirred for 2 hours at 60° C. and overnight at room temperature
  3. customThe crude product which crystallizes out
  4. filtrationis filtered off
  5. customrecrystallized from isopropanol

出典と根拠

ORDレコード
ord-50db3a5903ce4be8a71663d6af5a9e84
出典データセット
uspto-grants-1995_05
特許番号
US05416100

反応ノート

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