Phenylhydrazine → HCID 15886886, compound

HRID 651580Notes

Reaction equation

HRID 651580 reaction equation
[CH2:1]([N:7]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:8]([CH:10]1[CH2:19][C:18](=O)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[S:11]1)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:27]1([NH:33]N)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[CH2:1]([N:7]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:8]([CH:10]1[C:19]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[NH:33][C:18]=2[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[S:11]1)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

3

Reactant 2

HCID 7516PhenylhydrazineHCID 21709029HCID 21709029, compound

Product 1

HCID 15886886HCID 15886886, compound

Conditions

Temperature
170 °C

Procedure

N,N-Dihexyl-(4-oxo-thiochroman-2-yl)-carboxamide (1.00 g) and phenylhydrazine (0.26 ml) were stirred at 100° C. for 30 minutes, and the reaction mixture was dried under reduced pressure at 50° C. for 30 minutes. The residue, after addition of 1.44 g of anhydrous zinc chloride, was stirred at 170° C. for 5 minutes, and cooled to room temperature. To the reaction mixture was added ice water, followed by extracting with ethyl acetate. The extract was washed with 1N hydrochloric acid, a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the filtrate was concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give 0.79 g of N,N-dihexyl-6,11-dihydro-5-thia-11-aza-benzo[a]fluoren-6-carboxamide.

Workup

  1. customthe reaction mixture was dried under reduced pressure at 50° C. for 30 minutes
  2. additionThe residue, after addition of 1.44 g of anhydrous zinc chloride
  3. temperaturecooled to room temperature
  4. additionTo the reaction mixture was added ice water
  5. extractionby extracting with ethyl acetate
  6. washThe extract was washed with 1N hydrochloric acid
  7. dry with materiala saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate
  8. customAfter removal of the drying agent
  9. filtrationby filtration
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-b9cbada24e5e43cb84d2ff9b8eb10e10
Source dataset
uspto-grants-2001_08
Patent number
US06281355B1

Reaction notes

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