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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

HRID 373680
Notes
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Reaction equation

HRID 373680 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]=3
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 7672Phenyl isocyanateHCID 11107308(+)-7,8-dihydro-6,6-dimethyl-7-hydroxy-8-amino-6H-pyrano[2,3-f]benz-2,1,3-oxadiazole

Product 1

HCID 9819971(trans)-N-(7,8-Dihydro-7-hydroxy-6,6-dimethyl-6H-[1]benzopyrano[6,7-c][1,2,5]oxadiazol-8-yl)-N'-phenylureaYield 47.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent
HCID 7914
Diisopropyl Ether
Solvent

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

  1. temperatureThe reaction was heated
  2. temperatureat reflux for three hours
  3. customThe product slowly crystallized from solution
  4. filtrationIt was collected via suction filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-902cc5270e364a738f5cec5eec8abfd3
Source dataset
uspto-grants-1992_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05164509

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes