Methane → HCID 131711525, compound

HRID 237114

Reaction equation

HRID 237114 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([OH:16])[CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1.[Cl:17][C:18]1[C:23]([CH2:24]Cl)=[CH:22][N:21]=[C:20]2[N:26]([CH2:29][CH3:30])[N:27]=[CH:28][C:19]=12.C>O1CCCC1>[ClH:1].[Cl:17][C:18]1[C:23]([CH2:24][O:16][CH:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)=[CH:22][N:21]=[C:20]2[N:26]([CH2:29][CH3:30])[N:27]=[CH:28][C:19]=12

Participants

5

Reactant 3

HCID 297MethaneHCID 32238(+-)-alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanolHCID 21315243HCID 21315243, compound

Product 1

HCID 131711525HCID 131711525, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7.71 g. of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-ethanol (0.03 mol.) and 6.9 g. of 4-chloro-5-chloromethyl-1-ethyl-1H-pyrazolo[3,4-b]pyridine (0.03 mol.) are reacted according to the procedure of Example 1b. The combined tetrahydrofuran layers are treated with charcoal and filtered. Addition of 250 ml. of ether to the tetrahydrofuran solution separates an oily impurity which is removed by decanting the solution. After the solution containing the free base is cleared up by the addition of Hyflo filter aid there is added an excess of ethereal hydrochloric acid. The precipitated hydrochloride is allowed to stand for 2 hours, then filtered off, washed with ether and dried in a vacuum desiccator, yield: 8.3 g. (61%). The product is recrystallized from 3 N-hydrochloric acid with charcoal. The so obtained 4-chloro-5-[[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]-1-ethyl-1H-pyrazolo[3,4-b]-pyridine, hydrochloride (1:1) contains half a mole of water; m.p. 166°-167°.

Workup

  1. filtrationfiltered
  2. additionAddition of 250 ml
  3. customis removed
  4. customby decanting the solution
  5. additionAfter the solution containing the free base
  6. additionis cleared up by the addition of Hyflo
  7. filtrationfilter aid
  8. additionthere is added an excess of ethereal hydrochloric acid
  9. filtrationfiltered off
  10. washwashed with ether
  11. customdried in a vacuum desiccator, yield: 8.3 g
  12. customThe product is recrystallized from 3 N-hydrochloric acid with charcoal

Sources & evidence

ORD record
ord-34f3da7e7b8f4d08b7f67277317ce0e9
Source dataset
uspto-grants-1979_06
Patent number
US04159380

Linked notes

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