Sodium Chloride → HCID 21072524, compound

HRID 2105891Notes

Reaction equation

HRID 2105891 reaction equation
[OH-].[K+].[CH3:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9]Cl)=[CH:7][CH:6]=1.[CH:13]1[C:23]2[C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[CH2:20][C:19](=[O:28])[NH:18][C:17]=2[CH:16]=[CH:15][CH:14]=1.[Na+].[Cl-]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.ClCCl>[CH3:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][N:18]2[C:19](=[O:28])[CH2:20][C:21]3[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=3[C:23]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]2=3)=[CH:7][CH:6]=1

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 14797Potassium HydroxideHCID 699934-Methyloxybenzyl chlorideHCID 113677988-Azatricyclo[9.4.0.0,2,7]pentadeca-1(15),2,4,6,11,13-hexaen-9-one

Product 1

HCID 21072524HCID 21072524, compoundYield 107.2%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium bromide (0.82 g), potassium hydroxide (1.7 g) and p-methoxybenzylchloride (4.3 g), in that order, were added to a suspension of 5H,7H-dibenzo[b,d]azepin-6-one (5.63 g) in THF (112.5 mL). The reaction mixture was stirred 3 hours at room temperature. Dichloromethane (250 mL) and half-saturated aqueous NaCl (1500 mL) were added. The phases were separated, the organic phase was washed with half-saturated aqueous NaCl (1000 mL) and the aqueous layers were extracted with dichloromethane (150 mL) three times. The combined organic layers were dried (MgSO4), concentrated under reduced pressure and dried under high vacuum affording 5-(4-methoxy-benzyl)-5H,7H-dibenzo[b,d]azepin-6-one (9.5 g, quant.) as a brown oil, which was used in the next step without further purification.

Workup

  1. customThe phases were separated
  2. washthe organic phase was washed with half-saturated aqueous NaCl (1000 mL)
  3. extractionthe aqueous layers were extracted with dichloromethane (150 mL) three times
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-2d85a5006e19451ebc33a3d1603df04a
Source dataset
uspto-grants-2009_08
Patent number
US07579464B2

Reaction notes

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