Water → HCID 131712076, 화합물

HRID 1413102노트

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HRID 1413102 반응식
[OH-].[Na+].O.[Cl:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[CH:12]([OH:19])[CH2:13][N:14]1[CH:18]=[CH:17][N:16]=[CH:15]1.[Cl:20][C:21]1[N:25]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:24]=[C:23]([CH3:32])[C:22]=1[CH2:33]Cl>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.O1CCCC1>[ClH:4].[Cl:20][C:21]1[N:25]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:24]=[C:23]([CH3:32])[C:22]=1[CH2:33][O:19][CH:12]([C:6]1[CH:7]=[CH:8][C:9]([Cl:11])=[CH:10][C:5]=1[Cl:4])[CH2:13][N:14]1[CH:18]=[CH:17][N:16]=[CH:15]1

참가 물질

7

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HCID 962WaterHCID 14798Sodium HydroxideHCID 32238(+-)-alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanolHCID 49627755-chloro-4-(chloromethyl)-3-methyl-1-phenyl-1H-pyrazole

생성물 1

HCID 131712076HCID 131712076, 화합물

시약·촉매·용매 2

HCID 5963Benzyltrimethylammonium chloride촉매HCID 8028Tetrahydrofuran용매

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온도
45 °C

실험 절차

In a three-necked flask, fitted with stirrer, reflux condenser and gas inlet tube are introduced 24.3 g of sodium hydroxide (0.61 mol) and 23 ml of water. While passing nitrogen through the flask, the solution is cooled to 45° C. and then are added 6.5 g of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol (0.025 mol), 0.25 g of benzyltrimethyl-ammonium chloride and 40 ml of tetrahydrofuran. To the mixture, which is warmed to 50° C., are added 6.1 g of 5-chloro-4-chloromethyl-3-methyl-1-phenylpyrazole (0.025 mol). The mixture is stirred vigorously for 3 hours at 60° C. using a water bath. Then the warm mixture is transferred into a separating funnel, and the lower aqueous sodium hydroxide is extracted with 15 ml of tetrahydrofuran. The combined tetrahydrofuran layers are dried with sodium sulfate, trated with charcoal and distilled off to half of their volume. Addition of ether to the mixture causes a deposit of an oily side product. The clear solution (containing 5-chloro-4-[[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]-3-methyl-1-phenyl-1H-pyrazole) is decanted and after addition of ethereal hydrochloric acid, 9 g of 5-chloro-4-[[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-ethoxy]methyl]-3-methyl-1-phenyl-1H-pyrazole, hydrochloride (1:1) precipitate. Recrystallization from acetonitrile gives 6.9 g=55%, m.p. 184°-185° C.

후처리

  1. customIn a three-necked flask, fitted with stirrer
  2. temperaturereflux condenser and gas inlet tube
  3. temperatureTo the mixture, which is warmed to 50° C.
  4. customThen the warm mixture is transferred into a separating funnel
  5. extractionthe lower aqueous sodium hydroxide is extracted with 15 ml of tetrahydrofuran
  6. dry with materialThe combined tetrahydrofuran layers are dried with sodium sulfate
  7. distillationdistilled off to half of their volume
  8. additionAddition of ether to the mixture
  9. additionThe clear solution (containing 5-chloro-4-[[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]-3-methyl-1-phenyl-1H-pyrazole)
  10. customis decanted
  11. additionafter addition of ethereal hydrochloric acid, 9 g of 5-chloro-4-[[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-ethoxy]methyl]-3-methyl-1-phenyl-1H-pyrazole, hydrochloride (1:1) precipitate
  12. customRecrystallization from acetonitrile
  13. customgives 6.9 g=55%, m.p. 184°-185° C.

출처 및 근거

ORD 기록
ord-fdfe58401b394b2db47a8d7f6f36ab6b
출처 데이터셋
uspto-grants-1981_02
특허 번호
US04248881

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