Methanol → HCID 178431337, compound

HRID 1194383Notes

Reaction equation

HRID 1194383 reaction equation
[Na].Cl[C:3]1[CH:14]=[C:13]([CH:15]([C:17]2[N:18]=[CH:19][N:20](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:21]=2)[OH:16])[C:6]2[O:7][C:8]([CH3:12])([CH3:11])[O:9][CH2:10][C:5]=2[CH:4]=1.[Cl-].[NH4+].CO>N.C1(C)C=CC=CC=1>[CH3:11][C:8]1([CH3:12])[O:7][C:6]2[C:13]([CH:15]([C:17]3[N:18]=[CH:19][NH:20][CH:21]=3)[OH:16])=[CH:14][CH:3]=[CH:4][C:5]=2[CH2:10][O:9]1

Participants

7

Reactant 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 14520340HCID 14520340, compound

Product 1

HCID 178431337HCID 178431337, compoundYield 33.6%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 1140TolueneSolvent2×

Procedure

5.75 g (0.25 mole) of sodium are added piece by piece to a suspension of 21.46 g (0.04 mole) of alpha-(6-chloro-2,2-dimethyl-4H-1,3-benzodioxin-8-yl)-1-triphenylmethyl-1H-imidazole-4-methanol (prepared in Example 1.C.3.) in 2 liters of ammonia and 200 ml of toluene. stirring is maintained for 40 minutes, then the reaction mixture is decomposed by the addition of 6.42 g (0.12 mole) of ammonium chloride. 500 ml of toluene containing 10% of methanol are added thereto, the ammonia is evaporated and 500 ml of water are added thereto. The toluene phase is decanted off, dried over anhydrous sodium sulfate and then distilled. The residue, containing triphenylmethane, is partly dissolved in 50 ml of water containing 3.3 ml of concentrated hydrochloric acid and the suspension obtained is extracted with diethyl ether. The aqueous phase is subsequently adjusted to pH 8 by the addition of sodium bicarbonate, then extracted with dichloromethane. Subsequently, the solvent is removed by distillation to give 3.5 g of alpha-(2,2-dimethyl-4H-1,3-benzodioxin-8-yl)-1H-imidazole-4-methanol. Yield: 33% of theory. The product formed a hydrochloride (recrystallizable in a 1:1 v/v ethanol-diethyl ether mixture) which has a glassy appearance and which does not have a sharp melting point.

Workup

  1. temperatureis maintained for 40 minutes
  2. customthe ammonia is evaporated
  3. addition500 ml of water are added
  4. customThe toluene phase is decanted off
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationdistilled
  7. additionThe residue, containing triphenylmethane
  8. dissolutionis partly dissolved in 50 ml of water containing 3.3 ml of concentrated hydrochloric acid
  9. customthe suspension obtained
  10. extractionis extracted with diethyl ether
  11. additionThe aqueous phase is subsequently adjusted to pH 8 by the addition of sodium bicarbonate
  12. extractionextracted with dichloromethane
  13. customSubsequently, the solvent is removed by distillation

Sources & evidence

ORD record
ord-54d79d72811945b584620df9fd1cacec
Source dataset
uspto-grants-1989_03
Patent number
US04814343

Reaction notes

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