Water → HCID 131712076, compound

HRID 1413102Notes

Reaction equation

HRID 1413102 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

HCID 131712076HCID 131712076, compound

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

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.

Workup

  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.

Sources & evidence

ORD record
ord-fdfe58401b394b2db47a8d7f6f36ab6b
Source dataset
uspto-grants-1981_02
Patent number
US04248881

Reaction notes

Loading…