Toluene → HCID 14518413, compound

HRID 1723107Notes

Reaction equation

HRID 1723107 reaction equation
CC1C=CC=CC=1.[C:8]1([C:14]2[N:18]([CH2:19][CH2:20][CH3:21])[C:17]3[CH:22]=[CH:23][C:24]([C:26](OC)=[O:27])=[CH:25][C:16]=3[N:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Na+]>O>[C:8]1([C:14]2[N:18]([CH2:19][CH2:20][CH3:21])[C:17]3[CH:22]=[CH:23][C:24]([CH2:26][OH:27])=[CH:25][C:16]=3[N:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 1140Toluene2×HCID 14798Sodium HydroxideHCID 14518412HCID 14518412, compound

Product 1

HCID 14518413HCID 14518413, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(a-4) To a stirred and cooled (ice-bath) solution of 103.9 parts of sodium dihydro-bis(2-methoxyethoxy)aluminate in 45 parts of methylbenzene was added dropwise a solution of 88.5 parts of methyl 2-phenyl-1-propyl-1H-benzimidazole-5-carboxylate in 270 parts of methylbenzene. Upon completion, stirring was continued for 1 hour at room temperature. The reaction mixture was decomposed by the addition of a mixture of 200 parts of a sodium hydroxide solution 7.5 N and 200 parts of water. The methylbenzene-phase was separated, dried, filtered and evaporated. The residue was washed with 210 parts of 2,2'-oxybispropane. The product was filtered off and dried, yielding 73 parts (91%) of 2-phenyl-1-propyl-1H-benzimidazole-5-methanol; mp. 112.9° C. (int. 60).

Workup

  1. stirringUpon completion, stirring
  2. customThe methylbenzene-phase was separated
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. washThe residue was washed with 210 parts of 2,2'-oxybispropane
  7. filtrationThe product was filtered off
  8. customdried

Sources & evidence

ORD record
ord-e017a4b371054c728e0804a85114021d
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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