2-(Trifluoromethyl)phenyl isocyanate → 4-Hydroxy-3-(2'-trifluoromethylphenylcarbamoyl)coumarin

HRID 55333

Reaction equation

HRID 55333 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4](=[O:12])[CH:3]=1.[F:13][C:14]([F:25])([F:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]=[C:22]=[O:23]>C(N(CC)CC)C>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4](=[O:12])[C:3]=1[C:22](=[O:23])[NH:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:14]([F:13])([F:25])[F:24]

Participants

4

Reactant 2

HCID 167942-(Trifluoromethyl)phenyl isocyanateHCID 546829304-Hydroxycoumarin

Product 1

HCID 867507734-Hydroxy-3-(2'-trifluoromethylphenylcarbamoyl)coumarin

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

According to the procedure of example 17, 4-hydroxycoumarin (2.00 g. 12.8 mmol) and 2-trifluoromethylphenylisocyanate(1.93 ml, 12.8 mmol) were reacted in the presence of triethylamine (0.05 ml) to generate the title compound as an off-white solid, mp 157°-159°]C., (2.2 g, 6.30 mmol, 49.3%). Analysis: Calculated for C17H10NO4F3 : C, 58.45; H, 2.86; N, 4.01. Found: C, 58.47; H, 3.04; N, 4.02. 1H NMR (CDCl3): 8.06 (d, J=7.8 Hz, 2H), 7.70 (d, J=8.8 Hz, 2H), 7.62 (t, J=7.8 Hz, 1H), 7.38 (m, 3H).

Sources & evidence

ORD record
ord-ad90070a43b846dda8cfe0f2de2fa0e5
Source dataset
uspto-grants-1997_04
Patent number
US05624951

Linked notes

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