Sodium Chloride → HCID 76617925, compound

HRID 2105892Notes

Reaction equation

HRID 2105892 reaction equation
CC([O-])(C)C.[K+].[CH3:7][O:8][C:9]1[CH:31]=[CH:30][C:12]([CH2:13][N:14]2[C:20](=[O:21])[CH2:19][C:18]3[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=3[C:16]3[CH:26]=[CH:27][CH:28]=[CH:29][C:15]2=3)=[CH:11][CH:10]=1.C([O:37][N:38]=O)CC(C)C.[Na+].[Cl-]>C1COCC1.ClCCl>[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][N:14]2[C:20](=[O:21])[C:19](=[N:38][OH:37])[C:18]3[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=3[C:16]3[CH:26]=[CH:27][CH:28]=[CH:29][C:15]2=3)=[CH:30][CH:31]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 8053Isoamyl NitriteHCID 21072524HCID 21072524, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 76617925HCID 76617925, compoundYield 115.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Potassium tert-butylate (7.6 g) was added slowly to a solution of 5-(4-methoxy-benzyl)-5H,7H-dibenzo[b,d]azepin-6-one (14.6 g) in THF (146 mL) cooled to 0° C. After 10 minutes of stirring at 0° C., isopentylnitrite (10.6 g) was slowly added and the reaction mixture was further stirred for 105 minutes at 0° C. The reaction mixture was poured onto half-saturated aqueous NaCl (1200 mL), cooled to 0° C. and dichloromethane (500 mL) was added. The phases were separated, the organic phase was washed with half-saturated aqueous NaCl (1200 mL) and the aqueous layers were extracted with dichloromethane (250 mL) twice. The combined organic layers were dried (MgSO4), concentrated under reduced pressure and dried under high vacuum affording 5-(4-methoxy-benzyl)-5H-dibenzo[b,d]azepine-6,7-dione 7-oxime (18.4 g, quant.) as a yellow foam, which was used in the next step without further purification.

Workup

  1. stirringthe reaction mixture was further stirred for 105 minutes at 0° C
  2. temperaturecooled to 0° C.
  3. customThe phases were separated
  4. washthe organic phase was washed with half-saturated aqueous NaCl (1200 mL)
  5. extractionthe aqueous layers were extracted with dichloromethane (250 mL) twice
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-c2f8e8becc8442d3925a4e07ae17a9ad
Source dataset
uspto-grants-2009_08
Patent number
US07579464B2

Reaction notes

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