Phenyl isocyanate → HCID 9819354, compound

HRID 1609695Notes

Reaction equation

HRID 1609695 reaction equation
[NH2:1][C@@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[C:4]([CH3:15])([CH3:14])[C@H:3]1[OH:16].[C:17]1([N:23]=[C:24]=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)C>[OH:16][C@@H:3]1[C:4]([CH3:14])([CH3:15])[C:5]2[C:10](=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=2)[C@H:2]1[NH:1][C:24]([NH:23][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:25]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 67785604HCID 67785604, compound

Product 1

HCID 9819354HCID 9819354, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of trans-3-amino-1,1-dimethyl-2-hydroxy-5-nitro indane (0.75 g, 3.37 mmoles, as prepared in part H of Example 1) in refluxing ethanol (6 ml) was added phenyl isocyanate (0.40 g, 3.37 mmoles). The reaction mixture was heated at reflux for 3 hours and cooled to room temperature. The product, which had precipitated from solution, was collected via suction filtration and washed with isopropyl ether. In this manner 0.82 g of the title compound was obtained as a white solid, m.p. 194°-195° C. 1H NMR (DMSO-d6) δ 8.66 (s, 1H), 8.16 (d, J=8.79 Hz, 1H), 7.94 (s, 1H), 7.51 (m, 3H), 7.28 (m, 2H), 6.95 (m, 1H), 6.73 (d, J=7.62 Hz, 1H), 5.67 (d, J=5.28 Hz, 1H), 5.00 (t, J=8.21 Hz, 1H), 3.86 (dd, J=5.86 and 8.79 Hz, 1H), 1.36 (s, 3H), 1.09 (s, 3H). 13C NMR (DMSO-d6) δ 156.53, 155.75, 146.91, 142.36, 140.26, 128.74, 123.96, 123.47, 121.37, 118.63, 117.91, 84.71, 57.70, 44.11, 25.07, 22.42.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 hours
  3. customThe product, which had precipitated from solution
  4. filtrationwas collected via suction filtration
  5. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-102fa6b8532c427aa5f37f01b955caf0
Source dataset
uspto-grants-1995_03
Patent number
US05401848

Reaction notes

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