Ammonia → HCID 53733971, compound

HRID 2247916Notes

Reaction equation

HRID 2247916 reaction equation
[CH:1]([C:3]1[CH:8]=[C:7]([CH:9]([N:16]2[CH:20]=[CH:19][N:18]=[CH:17]2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4]=1[NH:21][C:22](=O)[CH3:23])=O.[NH3:25]>CO>[N:16]1([CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]2[CH:8]=[C:3]3[C:4](=[CH:5][CH:6]=2)[N:21]=[C:22]([CH3:23])[N:25]=[CH:1]3)[CH:20]=[CH:19][N:18]=[CH:17]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 54412810HCID 54412810, compound

Product 1

HCID 53733971HCID 53733971, compoundYield 14.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.2 parts of N-(2-formyl-4-[(1H-imidazol-1-yl)phenylmethyl]phenyl]acetamide and 40 parts of methanol, saturated with ammonia was stirred for 1 hour at room temperature. After evaporation, dichloromethane was added. The solution was filtered and the filtrate was evaporated. The residue was purified by column chromatography over silica gel first using a mixture of dichloromethane and methanol (97:3 by volume) and then a mixture of dichloromethane and methanol (94:6 by volume) as eluents. The eluent of the desired fraction was evaporated and the residue was crystallized from 21 parts of 1,1'-oxybisethane. The product was filtered off and dried, yielding 0.3 parts (14.7%) of 6-[(1H-imidazol-1-yl)phenylmethyl]-2-methylquinazoline; mp. 129.6° C.

Workup

  1. customAfter evaporation, dichloromethane
  2. additionwas added
  3. filtrationThe solution was filtered
  4. customthe filtrate was evaporated
  5. customThe residue was purified by column chromatography over silica gel
  6. additiona mixture of dichloromethane and methanol (97:3 by volume)
  7. additiona mixture of dichloromethane and methanol (94:6 by volume) as eluents
  8. customThe eluent of the desired fraction was evaporated
  9. customthe residue was crystallized from 21 parts of 1,1'-oxybisethane
  10. filtrationThe product was filtered off
  11. customdried

Sources & evidence

ORD record
ord-75492d2303164f6d8e11da5f97db8b70
Source dataset
uspto-grants-1991_08
Patent number
US05037829

Reaction notes

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