Ammonia → HCID 67491059, compound

HRID 1917400Notes

Reaction equation

HRID 1917400 reaction equation
[C:1]([NH:20][CH2:21][CH:22]1[C:27](=O)[CH2:26][CH2:25][CH2:24][O:23]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-]#N.[Na+].[Cl-].[NH4+:33].[C:34](=[O:37])([O-])[O-].[NH4+:38].[NH4+].N.[CH2:41]([OH:43])C>>[C:1]([NH:20][CH2:21][CH:22]1[O:23][CH2:24][CH2:25][CH2:26][C:27]21[NH:38][C:41](=[O:43])[NH:33][C:34]2=[O:37])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 6

HCID 222AmmoniaHCID 702EthanolHCID 8929Sodium CyanideHCID 25517Ammonium ChlorideHCID 517111Ammonium Carbonate2×HCID 67490982HCID 67490982, compound

Product 1

HCID 67491059HCID 67491059, compound

Conditions

Temperature
60 °C

Procedure

A mixture of 2-(tritylamino)methyl-5,6-dihydro-2H-pyran-3(4H)-one (9.56 g, 25.7 mmol), sodium cyanide (2.52 g, 51.4 mmol), ammonium chloride (2.75 g, 51.4 mmol), ammonium carbonate (10.18 g, 128.7 mmol), concentrated aqueous ammonia (50 mL), and ethanol (50 mL) was stirred in a nitrogen atmosphere on an oil bath at 60° C. for 4.5 hours. Ammonium carbonate (10.18 g, 128.7 mmol) was added, and the mixture was stirred at the same temperature for further 19.5 hours. The resulting reaction solution was concentrated under reduced pressure, and the residue was extracted with ethyl acetate (300 mL, 100 mL). Then, the organic layers were combined and washed with water (2×100 mL) and brine (100 mL). The resulting organic layer was dried over anhydrous magnesium sulfate and filtered. Then, the solvent was evaporated under reduced pressure to give 11.35 g (quantitative) of the title compound as a colorless amorphous.

Workup

  1. stirringthe mixture was stirred at the same temperature for further 19.5 hours
  2. customThe resulting reaction solution
  3. concentrationwas concentrated under reduced pressure
  4. extractionthe residue was extracted with ethyl acetate (300 mL, 100 mL)
  5. washwashed with water (2×100 mL) and brine (100 mL)
  6. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThen, the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d87f512e83624110aa792f71c14cb9dd
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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