Phenyl isocyanate → HCID 10091155, compound

HRID 1197690Notes

Reaction equation

HRID 1197690 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) δ 7.4 (s, 1 H), 7.32 (d, J=9.8 Hz, 1 H), 7.17 (m, 5 H), 7.0 (m, 1 H), 6.77 (d, J=8.2 Hz, 1 H), 5.22 (br d, 1H), 4.80 (br t, 1 H), 3.45 (d, J=9.4 Hz, 1 H), 1.37 (s, 3 H), 1.12 (s, 3 H); 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, 1647.8, 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-45384e25a4e744889327897b86fef0dd
Source dataset
uspto-grants-1994_01
Patent number
US05276168

Reaction notes

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