Phenol → HCID 19966717, compound

HRID 976222Notes

Reaction equation

HRID 976222 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:8]([C:11]1[N:16]=[C:15]([O:17][CH3:18])[CH:14]=[C:13]([C:19]([F:22])([F:21])[F:20])[N:12]=1)=[C:9]=[O:10]>C(Cl)Cl>[CH3:18][O:17][C:15]1[CH:14]=[C:13]([C:19]([F:20])([F:22])[F:21])[N:12]=[C:11]([NH:8][C:9]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:10])[N:16]=1

Participants

4

Reactant 2

HCID 996PhenolHCID 19966721HCID 19966721, compound

Product 1

HCID 19966717HCID 19966717, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.2 g of phenol (45 mmol) were added at 25° C. to a solution of 9.9 g of 2-isocyanato-4-methoxy-6-trifluoromethylpyrimidine (45 mmol) in 50 ml of methylene chloride. Stirring was carried out for 16 hours at 25° C., the methylene chloride was distilled off under reduced pressure and the residue was stirred vigorously with 100 ml of a diisopropyl ether/hexane mixture (v/v 1:20), whereupon crystallization occurred. The product was filtered off with suction and dried under reduced pressure from a water pump at 50° C. The title compound (12.2 g; 87% of theory) was obtained as colorless crystals of melting point 85°-88° C.

Workup

  1. distillationthe methylene chloride was distilled off under reduced pressure
  2. stirringthe residue was stirred vigorously with 100 ml of a diisopropyl ether/hexane mixture (v/v 1:20), whereupon crystallization
  3. filtrationThe product was filtered off with suction
  4. dry with materialdried under reduced pressure from a water pump at 50° C

Sources & evidence

ORD record
ord-2fb4122ac8214d9e93828070a846f1af
Source dataset
uspto-grants-1997_03
Patent number
US05612286

Reaction notes

Loading…