Phenyl isocyanate → (trans)-N-(7,8-Dihydro-7-hydroxy-6,6-dimethyl-6H-[1]benzopyrano[6,7-c][1,2,5]oxadiazol-8-yl)-N'-phenylurea
Reaction equation
[CH3:1][C:2]1([CH3:17])[O:14][C:6]2=[CH:7][C:8]3[C:9]([CH:13]=[C:5]2[CH:4]([NH2:15])[CH:3]1[OH:16])=[N:10][O:11][N:12]=3.[C:18]1([N:24]=[C:25]=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)C.C(OC(C)C)(C)C>[OH:16][C@H:3]1[C@H:4]([NH:15][C:25]([NH:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:26])[C:5]2=[CH:13][C:9]3[C:8]([CH:7]=[C:6]2[O:14][C:2]1([CH3:17])[CH3:1])=[N:12][O:11][N:10]=3Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 7,8-dihydro-6,6-dimethyl-7-hydroxy-8-amino-6H-pyrano[2,3-f]benzo-2,1,3-oxadiazole (0.25 g, 1.06 mmoles) (prepared as described in part I of Example 1) in ethanol (2.5 ml) at 60° C. was added phenyl isocyanate (0.126 g, 1.06 mmoles). The reaction was heated at reflux for three hours, cooled to room temperature and diluted with isopropyl ether (5 ml). The product slowly crystallized from solution. It was collected via suction filtration and dried under vacuum to obtain 0.18 g of the desired compound as a beige solid. The residue obtained upon evaporation of the mother liquor was chromatographed on silica gel eluting with 1:1 ethyl acetate/hexane to afford an additional 0.16 g of product. The two crops were combined and triturated with isopropyl ether to obtain 0.30 g of the title compound as an off-white solid (m.p. 215°-216° C.).
Workup
- temperatureThe reaction was heated
- temperatureat reflux for three hours
- customThe product slowly crystallized from solution
- filtrationIt was collected via suction filtration
- customdried under vacuum
Sources & evidence
- ORD record
- ord-902cc5270e364a738f5cec5eec8abfd3
- Source dataset
- uspto-grants-1992_11
- Patent number
- US05164509
Reaction notes
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