Ethanol → HCID 54387571, compound

HRID 2247915Notes

Reaction equation

HRID 2247915 reaction equation
[N:1]1([CH:6]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:18])OCC)=[C:9]([CH:19]=[N:20][CH3:21])[CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.C(O)C.[BH4-].[Na+]>CO>[N:1]1([CH:6]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:7]2[CH:8]=[C:9]3[C:10](=[CH:11][CH:12]=2)[NH:13][C:14](=[O:18])[N:20]([CH3:21])[CH2:19]3)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 54256715HCID 54256715, compound

Product 1

HCID 54387571HCID 54387571, compoundYield 20.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred mixture of 1.7 parts of ethyl [4-[(1H-imidazol-1-yl)phenylmethyl]-2-[(methylimino)methyl]phenyl]carbamate and 31.6 parts of ethanol were added 1 part of sodium tetrahydroborate (portionwise) and 55.3 parts of methanol. After stirring for 7 hours at 40°-50° C., the reaction mixture was evaporated. The residue was taken up in water (to which 0.29 parts of acetic acid were added) and the whole was basified with NH4OH. The product was extracted with dichloromethane and the extract was dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CHCl3 /CH3OH 95:5). The eluent of the desired fraction was evaporated and the residue was crystallized from ethyl acetate, yielding 0.3 parts (20.1%) of 3,4-dihydro-6-[(1H-imidazol-1-yl)phenylmethyl]-3-methyl-2(1H)-quinazolinone; mp. 173.8° C. (comp. 23).

Workup

  1. customthe reaction mixture was evaporated
  2. extractionThe product was extracted with dichloromethane
  3. customthe extract was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography (silica gel; CHCl3 /CH3OH 95:5)
  7. customThe eluent of the desired fraction was evaporated
  8. customthe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-df20c6e6ce66411dac515b5f27301063
Source dataset
uspto-grants-1991_08
Patent number
US05037829

Reaction notes

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