Trimethyl orthoformate → 7-[(1H-imidazol-1-yl)phenylmethyl]-4(3H)-quinazolinone

HRID 2247918Notes

Reaction equation

HRID 2247918 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([CH:11]([N:18]2[CH:22]=[CH:21][N:20]=[CH:19]2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[CH3:23]OC(OC)OC>C(O)=O>[N:18]1([CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[CH:10]=[C:2]3[C:3]([C:4](=[O:5])[NH:6][CH:23]=[N:1]3)=[CH:7][CH:8]=2)[CH:22]=[CH:21][N:20]=[CH:19]1

Participants

4

Reactant 2

HCID 9005Trimethyl orthoformateHCID 538753582-amino-4-[(1H-imidazol-1-yl)phenylmethyl]benzamide

Product 1

HCID 1359816527-[(1H-imidazol-1-yl)phenylmethyl]-4(3H)-quinazolinoneYield 23.6%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 4.2 parts of 2-amino-4-[(1H-imidazol-1-yl)phenylmethyl]benzamide, 97 parts of trimethoxymethane and 1.3 parts of formic acid was stirred for 5 hours at reflux temperature and overnight at room temperature. The solvent was evaporated and the residue was dissolved in methanol. The solution was basified with ammonious methanol and then evaporated. The residue was purified twice by column chromatography (silica gel; CHCl3 /CH3OH 95:5; CHCl3 /CH3OH 90:10). The eluent of the desired fraction was evaporated and the residue was crystallized from acetonitrile. The product was filtered off, washed with 2,2'-oxybispropane and dried, yielding 1 part (23.6%) of 7-[(1H-imidazol-1-yl)phenylmethyl]-4(3H)-quinazolinone; mp. 205.0° C. (comp. 47).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in methanol
  3. customevaporated
  4. customThe residue was purified twice by column chromatography (silica gel; CHCl3 /CH3OH 95:5; CHCl3 /CH3OH 90:10)
  5. customThe eluent of the desired fraction was evaporated
  6. customthe residue was crystallized from acetonitrile
  7. filtrationThe product was filtered off
  8. washwashed with 2,2'-oxybispropane
  9. customdried

Sources & evidence

ORD record
ord-c45ecfedfefa4869809a3651c02319cc
Source dataset
uspto-grants-1991_08
Patent number
US05037829

Reaction notes

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