Hydrochloric Acid → N-(4-hydroxy-3,5-dimethoxyphenyl)-N'-[4-(2-methylphenyl)-2-oxo-2,6,7,8-tetrahydrocyclopenta[g][1]benzopyran-3-yl]urea

HRID 36924Notes

Reaction equation

HRID 36924 reaction equation
C([O:4][C:5]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([NH:13][C:14]([NH:16][C:17]2[C:18](=[O:37])[O:19][C:20]3[CH:33]=[C:32]4[CH2:34][CH2:35][CH2:36][C:31]4=[CH:30][C:21]=3[C:22]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])=[O:15])=[CH:7][C:6]=1[O:38][CH3:39])(=O)C.Cl>O1CCCC1>[OH:4][C:5]1[C:6]([O:38][CH3:39])=[CH:7][C:8]([NH:13][C:14]([NH:16][C:17]2[C:18](=[O:37])[O:19][C:20]3[CH:33]=[C:32]4[CH2:34][CH2:35][CH2:36][C:31]4=[CH:30][C:21]=3[C:22]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])=[O:15])=[CH:9][C:10]=1[O:11][CH3:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15231610N-(4-acetoxy-3,5-dimethoxyphenyl)-N'-[4-(2-methylphenyl)-2-oxo-2,6,7,8-tetrahydrocyclopenta[g] [1]benzopyran-3-yl]urea

Product 1

HCID 15231602N-(4-hydroxy-3,5-dimethoxyphenyl)-N'-[4-(2-methylphenyl)-2-oxo-2,6,7,8-tetrahydrocyclopenta[g][1]benzopyran-3-yl]ureaYield 89.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(4-acetoxy-3,5-dimethoxyphenyl)-N'-[4-(2-methylphenyl)-2-oxo-2,6,7,8-tetrahydrocyclopenta[g] [1]benzopyran-3-yl]urea (400 mg) in tetrahydrofuran (4 ml) was added 10% methanolic hydrochloride (4 ml). The mixture was stirred at room temperature for 8 hours and the solvent was then distilled off. The residue was diluted with water and extracted with ethyl acetate. The extract was washed with water, dried (MgSO4) and distilled to remove the solvent. To the residue was added ethanol to give crystals of N-(4-hydroxy-3,5-dimethoxyphenyl)-N'-[4-(2-methylphenyl)-2-oxo-2,6,7,8-tetrahydrocyclopenta [g] [1]benzopyran-3-yl]urea (330 mg, 66.7%). Recrystallization from ethanol gave colorless needles, m.p. 176°-179° C.

Workup

  1. distillationthe solvent was then distilled off
  2. additionThe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried (MgSO4)
  6. distillationdistilled
  7. customto remove the solvent
  8. additionTo the residue was added ethanol

Sources & evidence

ORD record
ord-1d123b20df75436291fe46ad98200d5f
Source dataset
uspto-grants-1995_05
Patent number
US05418239

Reaction notes

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