Water → HCID 18626294, compound

HRID 1859747Notes

Reaction equation

HRID 1859747 reaction equation
C[O:2][C:3]1[CH:17]=[CH:16][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:8])=[CH:5][C:4]=1[NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>ClCCCl>[OH:2][C:3]1[CH:17]=[CH:16][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:8])=[CH:5][C:4]=1[NH:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 962WaterHCID 10543586HCID 10543586, compound

Product 1

HCID 18626294HCID 18626294, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Boron tribromide-dimethyl sulfide complex (3.1 g, 9.9 mmol) was added to a stirred suspension of 4-methoxy-3-phenylamino-N-phenyl-benzamide from Example 28 (0.9 g, 2.8 mmol) in 1,2-dichloroethane (50 mL) under an inert atmosphere, and the mixture heated to reflux. After 1.5 hours, the mixture was allowed to cool and was poured into water (125 mL) and extracted with dichloromethane (2×75 mL). The combined extracts were washed with water, then saturated brine, and dried over MgSO4. The solvent was removed under reduced pressure and the residue dissolved in ethyl acetate and filtered through a short column of silica gel. The filtrate was stripped of solvent and the residue recrystallized from toluene to afford the product (0.3 g); m.p. 158-159° C.

Workup

  1. temperaturethe mixture heated to reflux
  2. temperatureto cool
  3. extractionextracted with dichloromethane (2×75 mL)
  4. washThe combined extracts were washed with water
  5. dry with materialsaturated brine, and dried over MgSO4
  6. customThe solvent was removed under reduced pressure
  7. dissolutionthe residue dissolved in ethyl acetate
  8. filtrationfiltered through a short column of silica gel
  9. customthe residue recrystallized from toluene

Sources & evidence

ORD record
ord-cf72cd8e7ed1477e8df2c266e2b31c71
Source dataset
uspto-grants-2003_03
Patent number
US06528528B2

Reaction notes

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