Ammonium Chloride → HCID 14307646, compound

HRID 868263Notes

Reaction equation

HRID 868263 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([CH2:7][C:8]2[O:9][C:10]3[C:17](=[O:18])[CH:16]=[C:15]([CH2:19][CH2:20][CH3:21])[C:14](=[O:22])[C:11]=3[C:12]=2[CH3:13])=[CH:5][CH:4]=1.[NH4+].[Cl-].[N-:27]=[N+]=[N-].[Na+]>CO>[NH2:27][C:16]1[C:17](=[O:18])[C:10]2[O:9][C:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:24][CH:23]=3)=[C:12]([CH3:13])[C:11]=2[C:14](=[O:22])[C:15]=1[CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 14257811HCID 14257811, compound

Product 1

HCID 14307646HCID 14307646, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(4-methoxybenzyl)-3-methyl-5-propyl-4,7-benzofurandione (from Example 28) (295 mg, 0.91 mmol) in MeOH (3 mL) were added NH4Cl (109 mg) and NaN3 (130 mg). The mixture was heated to reflux for 4 hours and the solvent was then removed in vacuo. Water was added and the product was extracted into CH2Cl2 and chromatographed on silica gel (15% EtOAc/hexane) to give the title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 hours
  3. customthe solvent was then removed in vacuo
  4. additionWater was added
  5. extractionthe product was extracted into CH2Cl2
  6. customchromatographed on silica gel (15% EtOAc/hexane)

Sources & evidence

ORD record
ord-0ce48e3710914caca2b84401d2a31fd0
Source dataset
uspto-grants-1988_10
Patent number
US04778805

Reaction notes

Loading…