Isopropylamine → 4-{[(Propan-2-yl)amino]methylidene}-1-benzoxepine-3,5(2H,4H)-dione

HRID 1730086Notes

Reaction equation

HRID 1730086 reaction equation
Br[CH2:2][C:3]([C:5]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[O:7][CH:6]=1)=[O:4].[CH:16]([NH2:19])([CH3:18])[CH3:17].C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[CH3:17][CH:16]([NH:19][CH:6]=[C:5]1[C:14](=[O:15])[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[O:7][CH2:2][C:3]1=[O:4])[CH3:18]

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 11430Potassium CarbonateHCID 214864043-(Bromoacetyl)-4H-1-benzopyran-4-one

Product 1

HCID 542435574-{[(Propan-2-yl)amino]methylidene}-1-benzoxepine-3,5(2H,4H)-dioneYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 8.0g (0.03 mole) of 3-(bromoacetyl)chromone, 3.78g (0.064 mole) of isopropylamine, 200ml of methylene chloride and 30g of powdered anhydrous potassium carbonate was stirred at room temperature for 4 hours. The solids were filtered and the dark filtrate was filtered through layer of silica gel. This filtrate was concentrated to dryness. Recrystallization from ether gave 5.0g (68%) of product; m.p. 89°-91°. Recrystallization from isopropyl ether gave pure product; m.p. 92°-93°.

Workup

  1. filtrationThe solids were filtered
  2. filtrationthe dark filtrate was filtered through layer of silica gel
  3. concentrationThis filtrate was concentrated to dryness
  4. customRecrystallization from ether

Sources & evidence

ORD record
ord-b62c101384dd400ca5a1e8d0b10764c9
Source dataset
uspto-grants-1976_11
Patent number
US03991082

Reaction notes

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