Water → 1-(p-toluenesulfonyl)-5-ethoxycarbonylmethylidene-2,3,4,5-tetrahydro-1H-benzazepine

HRID 1870245Notes

Reaction equation

HRID 1870245 reaction equation
[H-].[Na+].[C:3]1([CH3:24])[CH:8]=[CH:7][C:6]([S:9]([N:12]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[C:16](=O)[CH2:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[OH2:25].[O:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1>>[C:3]1([CH3:24])[CH:8]=[CH:7][C:6]([S:9]([N:12]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[C:16](=[CH:28][C:27]([O:26][CH2:30][CH3:29])=[O:25])[CH2:15][CH2:14][CH2:13]2)(=[O:10])=[O:11])=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 2668521-Tosyl-3,4-dihydro-1H-benzo[b]azepin-5(2H)-one

Product 1

HCID 541408341-(p-toluenesulfonyl)-5-ethoxycarbonylmethylidene-2,3,4,5-tetrahydro-1H-benzazepine

Procedure

To a suspension of 60% NaH (33.8 g) in tetrahydrofuran (2 liters) is added dropwise triethylphosphonoacetate (189 ml) under ice-cooling, and the mixture is stirred at room temperature for 1.5 hour. To the mixture is added 1-(p-toluenesulfonyl)-5-oxo-2,3,4,5-tetrahydro-1H-benzazepine (150 g) in portions at room temperature, and the mixture is stirred at 50° C. for 8 hours. To the reaction solution is added water, and the mixture is extracted three time with ethyl acetate. The organic layer is washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting crystals are collected by filtration, washed with n-hexane, and dried to give 1-(p-toluenesulfonyl)-5-ethoxycarbonylmethylidene-2,3,4,5-tetrahydro-1H-benzazepine (170.4 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred at 50° C. for 8 hours
  3. extractionthe mixture is extracted three time with ethyl acetate
  4. washThe organic layer is washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. filtrationThe resulting crystals are collected by filtration
  8. washwashed with n-hexane
  9. customdried

Sources & evidence

ORD record
ord-7dfa7417b43c4de19b75f7fed27048a7
Source dataset
uspto-grants-2000_08
Patent number
US06096736

Reaction notes

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