Triethylamine → N-(2,6-Dimethoxyphenyl)-N'-[3-(2-methylphenyl)-6,7-dihydro-5H-indeno[5,6-b]furan-2-yl]urea

HRID 488869

Reaction equation

HRID 488869 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[CH:22]=[C:21]3[C:17]([CH2:18][CH2:19][CH2:20]3)=[CH:16][C:10]=2[O:11][C:12]=1C(O)=O.C([N:25]([CH2:28]C)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:37])=CC=1.[CH3:47][O:48][C:49]1[CH:55]=[CH:54][CH:53]=[C:52]([O:56][CH3:57])[C:50]=1[NH2:51]>C1C=CC=CC=1.C(Cl)(Cl)Cl.O>[CH3:57][O:56][C:52]1[CH:53]=[CH:54][CH:55]=[C:49]([O:48][CH3:47])[C:50]=1[NH:51][C:28]([NH:25][C:12]1[O:11][C:10]2[CH:16]=[C:17]3[C:21](=[CH:22][C:9]=2[C:8]=1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1])[CH2:20][CH2:19][CH2:18]3)=[O:37]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 95940Benzenamine, 2,6-dimethoxy-HCID 199401P,P-Diphenylphosphinic azideHCID 222672623-(2-methylphenyl)-6,7-dihydro-5H-indeno[5,6-b]furan-2-carboxylic acid

Product 1

HCID 22267241N-(2,6-Dimethoxyphenyl)-N'-[3-(2-methylphenyl)-6,7-dihydro-5H-indeno[5,6-b]furan-2-yl]ureaYield 53%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A solution of 3-(2-methylphenyl)-6,7-dihydro-5H-indeno[5,6-b]furan-2-carboxylic acid (3 g), triethylamine (2.2 ml) and DPPA (2.9 ml) in benzene (200 ml) was stirred at room temperature for 1 hour, and then heated under reflux for 1 hour. After cooling to room temperature, to the reaction solution 2,6-dimethoxyaniline (1.6 g) was added and then heated under reflux for 1 hour. The reaction solution was combined with water and chloroform, and the organic layer was washed with diluted hydrochloric acid followed by a saturated aqueous solution of sodium hydrogen carbonate and water, and after drying over magnesium sulfate, the solvent was distilled off under reduced pressure. The resultant residue was purified by a silica gel column chromatography (eluent: chloroform), and further purified by recrystallization from THF-chloroform to obtain the title compound as a colorless crystal (2.4 g, 53%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 hour
  3. additionwas added
  4. temperatureheated
  5. temperatureunder reflux for 1 hour
  6. washthe organic layer was washed with diluted hydrochloric acid
  7. dry with materialafter drying over magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe resultant residue was purified by a silica gel column chromatography (eluent: chloroform)
  10. customfurther purified by recrystallization from THF-chloroform

Sources & evidence

ORD record
ord-b35e94050b9f47b4ab65992c20413b5e
Source dataset
uspto-grants-2005_12
Patent number
US06974806B2

Linked notes

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