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

HRID 36622노트

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HRID 36622 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

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온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-50db3a5903ce4be8a71663d6af5a9e84
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05416100

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