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 258032Notes

Reaction equation

HRID 258032 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-2d05187a96c348e1aaa8132cfe777fc1
Source dataset
uspto-grants-1993_11
Patent number
US05264454

Reaction notes

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