Hydrochloric Acid → 4-(Anilinomethylidene)-1-benzoxepine-3,5(2H,4H)-dione

HRID 1730088Notes

Reaction equation

HRID 1730088 reaction equation
[OH:1][C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][CH2:5][C:4](=[O:13])[C:3]=1[CH:14]=O.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl>CCOCC>[C:17]1([NH:16][CH:14]=[C:3]2[C:2](=[O:1])[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[O:6][CH2:5][C:4]2=[O:13])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 178519899HCID 178519899, compound

Product 1

HCID 539620654-(Anilinomethylidene)-1-benzoxepine-3,5(2H,4H)-dioneYield 58%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A quantity of 10.0g (0.049 mole) of 2,3-dihydro-5-hydroxy-3-oxo-1-benzoxepin-4-carboxaldehyde was added to 15g of aniline. The temperature rose to 45° as most solid went into solution. The dark mixture was heated at 105°-110° for 10 minutes and cooled. Ether (500ml) and 300ml of cold 2N hydrochloric acid were added, and the mixture was stirred for 5 minutes. The entire mixture was filtered to remove the dark, suspended insolubles. The ether phase of the filtrate was washed well with water, dried (Na2SO4) and concentrated to give 8.0g (58%) of crude product; m.p. 94°-96°. Recrystallization from ethyl acetate gave pure, orange-tan crystals; m.p. 98°-100°.

Workup

  1. customrose to 45° as most solid
  2. temperatureThe dark mixture was heated at 105°-110° for 10 minutes
  3. temperaturecooled
  4. filtrationThe entire mixture was filtered
  5. customto remove the dark
  6. washThe ether phase of the filtrate was washed well with water
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-19b2691799ef47328a0b63bd1ef9f983
Source dataset
uspto-grants-1976_11
Patent number
US03991082

Reaction notes

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