Sodium Carbonate → HCID 131716776, compound

HRID 704741Notes

Reaction equation

HRID 704741 reaction equation
C(O)(=O)/C=[CH:3]/[C:4]([OH:6])=[O:5].[NH:9]1[CH2:15][CH2:14][CH2:13][CH:12]([NH:16][C:17]2[N:21]([CH2:22][C:23]3[O:24][C:25]([CH3:28])=[CH:26][CH:27]=3)[C:20]3[CH:29]=[CH:30][CH:31]=[CH:32][C:19]=3[N:18]=2)[CH2:11][CH2:10]1.[C:33](=[O:36])([O-:35])[O-].[Na+].[Na+]>CO>[C:4]([OH:6])(=[O:5])[C:33]([OH:35])=[O:36].[CH3:28][C:25]1[O:24][C:23]([CH2:22][N:21]2[C:20]3[CH:29]=[CH:30][CH:31]=[CH:32][C:19]=3[N:18]=[C:17]2[NH:16][CH:12]2[CH2:13][CH2:14][CH2:15][N:9]([CH2:3][CH2:4][OH:5])[CH2:10][CH2:11]2)=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 131716769HCID 131716769, compound

Product 1

HCID 131716776HCID 131716776, compoundYield 6.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of 11.3 parts of N-(hexahydro-1H-azepin-4-yl)-1-[(5-methyl-2-furanyl)methyl]-1H-benzimidazol-2-amine (E)-2-butenedioate(2:3), hemihydrate, 10.6 parts of sodium carbonate and 120 parts of methanol was stirred for 30 minutes at reflux temperature. After cooling to 30° C., gaseous oxirane was bubbled during 2 hours through the mixture. The reaction mixture was evaporated and the residue was stirred in dichloromethane. The precipitate was filtered off over diatomaceous earth and the filtrate was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane, methanol and ammonium hydroxide (90:9:1 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the ethanedioate salt in 2-propanone. The salt was filtered off and crystallized from a mixture of 2-propanone and ethanol. The product was filtered off and dried, yielding 0.7 parts (6.3%) of hexahydro-4-[[1-[(5-methyl-2-furanyl)methyl]-1H-benzimidazol-2-yl]amino]-1H-azepine-1-ethanol ethanedioate(1:2); mp. 155.8° C. (compound 211).

Workup

  1. temperatureat reflux temperature
  2. customgaseous oxirane was bubbled during 2 hours through the mixture
  3. customThe reaction mixture was evaporated
  4. stirringthe residue was stirred in dichloromethane
  5. filtrationThe precipitate was filtered off over diatomaceous earth
  6. customthe filtrate was evaporated
  7. customThe residue was purified by column chromatography over silica gel using
  8. additiona mixture of trichloromethane, methanol and ammonium hydroxide (90:9:1 by volume) as eluent
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated
  11. filtrationThe salt was filtered off
  12. customcrystallized from a mixture of 2-propanone and ethanol
  13. filtrationThe product was filtered off
  14. customdried

Sources & evidence

ORD record
ord-88bea1c4ce6a44ffa51125bba03a8c36
Source dataset
uspto-grants-1991_01
Patent number
US04988689

Reaction notes

Loading…