Ethanol → HCID 14518380, compound

HRID 1723098Notes

Reaction equation

HRID 1723098 reaction equation
[Na].Cl.[OH:3][N:4]1[C:8]2[CH:9]=[C:10]([CH2:13][OH:14])[CH:11]=[CH:12][C:7]=2[N:6]=[C:5]1[C:15]([O:17][CH2:18][CH3:19])=[O:16].[CH2:20](O)C>>[OH:14][CH2:13][C:10]1[CH:11]=[CH:12][C:7]2[N:6]=[C:5]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:4]([O:3][CH3:20])[C:8]=2[CH:9]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 5360545SodiumHCID 14518377HCID 14518377, compound

Product 1

HCID 14518380HCID 14518380, compoundYield 50%

Procedure

(a-4) To a stirred soluiton of 0.92 parts of sodium in 32 parts of ethanol were added 5.46 parts of ethyl 1-hydroxy-6-(hydroxymethyl)-1H-benzimidazole-2-carboxylate monohydrochloride. The whole was stirred for 10 minutes and concentrated. 18 Parts of methylbenzene were added and the mixture was evaporated. 13.5 Parts of N,N-dimethylformamide and a solution of 2.84 parts of iodomethane in 4.5 parts of N,N-dimethylformamide were added. After stirring for 30 minutes, the reaction mixture was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and acetonitrile (80:20 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of 2-propanol and 2,2'-oxybispropane (1:4 by volume). The product was filtered off and dried, yielding 2.5 parts (50%) of ethyl 6-(hydroxymethyl)-1-methoxy-1H-benzimidazole-2-carboxylate; mp. 110.1° C. (int. 32).

Workup

  1. concentrationconcentrated
  2. addition18 Parts of methylbenzene were added
  3. customthe mixture was evaporated
  4. addition13.5 Parts of N,N-dimethylformamide and a solution of 2.84 parts of iodomethane in 4.5 parts of N,N-dimethylformamide were added
  5. stirringAfter stirring for 30 minutes
  6. customthe reaction mixture was evaporated
  7. customThe residue was purified by column chromatography over silica gel using
  8. additiona mixture of trichloromethane and acetonitrile (80:20 by volume) as eluent
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated
  11. customThe residue was crystallized from a mixture of 2-propanol and 2,2'-oxybispropane (1:4 by volume)
  12. filtrationThe product was filtered off
  13. customdried

Sources & evidence

ORD record
ord-43b21e7ab5a94d489f976cdef7ab3a16
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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