Benzyl Alcohol → HCID 21706541, compound

HRID 1387290Notes

Reaction equation

HRID 1387290 reaction equation
C([C:4]1[C:5](=[O:20])[N:6]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[N:7]=[CH:8][C:9]=1[CH3:10])(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:28])C=CC=CC=1.C([N:40]([CH2:43]C)CC)C.[CH2:45]([OH:52])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>C1C=CC=CC=1>[CH2:45]([O:52][C:43]([NH:40][C:4]1[C:5](=[O:20])[N:6]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)[N:7]=[CH:8][C:9]=1[CH3:10])=[O:28])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 21706485HCID 21706485, compound

Product 1

HCID 21706541HCID 21706541, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred solution of 4-carboxy-2-(4-methoxybenzyl)-5-methyl-3-pyridazinone (0.50 g, 1.8 mmol) in benzene (20 mL) was added diphenylphosphoryl azide (0.63 g, 2.3 mmol) and triethylamine (0.76 mL, 5.5 mmol). The mixture was stirred at rt for 30 minutes, heated under reflux for 30 minutes, and cooled. Benzyl alcohol (0.24 g, 2.2 mmol) was added, and the mixture was heated under reflux for 17 hours. The mixture was cooled, washed with aqueous citric acid, water, aqueous sodium bicarbonate and brine, dried, filtered and evaporated. Chromatography of the residue over silica gel (15% to 25% ethyl acetate/hexane) gave 4-benzyloxycarbonylamino-2-(4-methoxybenzyl)-5-methyl-3-pyridazinone (0.39 g, 1.0 mmol, 56%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 30 minutes
  3. temperaturecooled
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 17 hours
  6. temperatureThe mixture was cooled
  7. washwashed with aqueous citric acid, water, aqueous sodium bicarbonate and brine
  8. customdried
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-f7fdcf39ca3a48d391221fc97eb37a06
Source dataset
uspto-grants-2001_07
Patent number
US06268365B1

Reaction notes

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