1-(triphenylmethyl)-1H-imidazole-4-carbaldehyde → alpha-(4H-1,3-Benzodioxin-6-yl)-1-triphenylmethyl-1H-imidazole-4-methanol

HRID 1194370Notes

Reaction equation

HRID 1194370 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]2[O:6][CH2:7][O:8][CH2:9][C:4]=2[CH:3]=1.[C:12]1([C:18]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:19]2[CH:23]=[C:22]([CH:24]=[O:25])[N:21]=[CH:20]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[O:6]1[C:5]2[CH:10]=[CH:11][C:2]([CH:24]([C:22]3[N:21]=[CH:20][N:19]([C:18]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH:23]=3)[OH:25])=[CH:3][C:4]=2[CH2:9][O:8][CH2:7]1

Participants

3

Reactant 2

HCID 6182331-(triphenylmethyl)-1H-imidazole-4-carbaldehydeHCID 145203376-Bromo-4H-1,3-benzodioxine

Product 1

HCID 14520344alpha-(4H-1,3-Benzodioxin-6-yl)-1-triphenylmethyl-1H-imidazole-4-methanolYield 53%

Procedure

This compound is prepared like the preceding compound but starting from 6-bromo-4H-1,3-benzodioxin and 1-triphenylmethyl-1H-imidazole-4-carboxaldehyde. After decomposing the reaction mixture, the reaction product is extracted with dichloromethane and recrystallized from isopropyl alcohol. By chromatography of the residue obtained after evaporation of the mother liquors, there is obtained a second crop of product. Yield: 53% of theory; M.P.: 165°-167° C.

Workup

  1. customThis compound is prepared like the preceding compound
  2. extractionthe reaction product is extracted with dichloromethane
  3. customrecrystallized from isopropyl alcohol
  4. customBy chromatography of the residue obtained
  5. customafter evaporation of the mother liquors
  6. customthere is obtained a second crop of product

Sources & evidence

ORD record
ord-8522ab1a0ab442ca861b3c58720b5f57
Source dataset
uspto-grants-1989_03
Patent number
US04814343

Reaction notes

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