Hydrochloric Acid → 4-Hydroxy-3-(4-trifluoromethyloxyphenyl-carbamoyl)-coumarin

HRID 35267

Reaction equation

HRID 35267 reaction equation
C(N(CC)CC)C.[F:8][C:9]([F:21])([F:20])[O:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]=[C:18]=[O:19])=[CH:13][CH:12]=1.[OH:22][C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[O:26][C:25](=[O:33])[CH:24]=1.Cl>CS(C)=O.O>[OH:22][C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[O:26][C:25](=[O:33])[C:24]=1[C:18](=[O:19])[NH:17][C:14]1[CH:13]=[CH:12][C:11]([O:10][C:9]([F:20])([F:21])[F:8])=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 92298p-(Trifluoromethoxy)phenyl isocyanateHCID 546829304-Hydroxycoumarin

Product 1

HCID 546938814-Hydroxy-3-(4-trifluoromethyloxyphenyl-carbamoyl)-coumarinYield 45.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

First 5.1 g (0.05 mol) of triethylamine and then, slowly, 10.2 g (0.05 mol) of 4-trifluoromethoxyphenyl isocyanate are added dropwise to 8.1 g (0.05 mol) of 4-hydroxycoumarin in 100 ml of dimethylsulphoxide at room temperature. The temperature thereby rises to 31° C. The reaction mixture is subsequently stirred at room temperature for 5 hours. It is added to a mixture of 250 ml of cold water and 15 ml of concentrated hydrochloric acid, whereupon a white precipitate separates out. The mixture is stirred for 30 minutes, with cooling, and the precipitate is filtered off with suction, rinsed with acid water and dried at 50° C. in vacuo. Recrystallization from 100 ml of dioxane gives 8.3 g (45.6% of theory) of 4-hydroxy-3-(4-trifluoromethyloxyphenyl-carbamoyl)-coumarin of melting point 194°-195° C.

Workup

  1. customthereby rises to 31° C
  2. stirringThe mixture is stirred for 30 minutes
  3. temperaturewith cooling
  4. filtrationthe precipitate is filtered off with suction
  5. washrinsed with acid water
  6. customdried at 50° C. in vacuo
  7. customRecrystallization from 100 ml of dioxane

Sources & evidence

ORD record
ord-268688d9dcef4871bc52a521b549d8f2
Source dataset
uspto-grants-1988_08
Patent number
US04766144

Linked notes

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