Phenyl isocyanate → HCID 10091155, compound

HRID 129184Notes

Reaction equation

HRID 129184 reaction equation
[NH2:1][C@@H:2]1[C:7]2[CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=[CH:11][C:6]=2[O:5][C:4]([CH3:17])([CH3:16])[C@H:3]1[OH:18].[C:19]1([N:25]=[C:26]=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)C>[OH:18][C@H:3]1[C@H:2]([NH:1][C:26]([NH:25][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:27])[C:7]2[CH:8]=[C:9]([C:12]([F:15])([F:13])[F:14])[CH:10]=[CH:11][C:6]=2[O:5][C:4]1([CH3:16])[CH3:17]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 67809980HCID 67809980, compound

Product 1

HCID 10091155HCID 10091155, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of (trans)-4-amino-3,4-dihydro-3-hydroxy-2,2-dimethyl-6-trifluoromethyl-2H-1-benzopyran (0.5 g, 1.9 mmol) (prepared according to D. R. Buckle et al., J. Med. Chem., 1990, 33, p. 3028) in ethanol (5 ml) under argon was treated with phenylisocyanate (0.23 g, 1.9 mmol) and the reaction was heated at reflux temperature for 4 hours. The product precipitated out of the reaction. The reaction was then concentrated in vacuo and the residue was triturated with isopropyl ether and hexanes to give the title compound as a colorless solid (0.5 g), m.p. 174°-175° C.: 1H NMR (CDCl3) δ7.4 (s, 1H), 7.32 (d, J=9.8 Hz, 1H), 7.17 (m, 5H), 7.0 (m, 1H), 6.77 (d, J=8.2 Hz, 1H), 5.22 (br d, 1H), 4.80 (br t, 1H), 3.45 (d, J=9.4 Hz, 1H), 1.37 (s, 3H), 1.12 (s, 3H); 13C NMR (CDCl3) 157.0, 156.5, 139.1, 137.3, 129.4, 126.5, 125.0, 124.7, 122.0, 121.7, 118.0, 79.6, 76.4, 51.4, 26.3, 18.2; IR (KBr) 1118.5, 1264.8, 1332.1, 1443.4, 1500.9, 1558.3, 1598.8, 16477.8, 2981.4, 3391.3 cm-1.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux temperature for 4 hours
  3. customThe product precipitated out of the reaction
  4. concentrationThe reaction was then concentrated in vacuo
  5. customthe residue was triturated with isopropyl ether and hexanes

Sources & evidence

ORD record
ord-465520ada6254b2ba35248801fef978c
Source dataset
uspto-grants-1995_11
Patent number
US05466817

Reaction notes

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