(Diethylamino)sulfur trifluoride → 8-chloro-5-(4-chlorophenyl)-5-fluoro-5H-indeno[1,2-d]pyrimidine

HRID 622101Notes

Reaction equation

HRID 622101 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)(O)[C:7]3[CH:12]=[N:11][CH:10]=[N:9][C:8]=32)=[CH:4][CH:3]=1.C(N(S(F)(F)[F:29])CC)C.C(=O)(O)[O-].[K+]>C(Cl)Cl>[Cl:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)([F:29])[C:7]3[CH:12]=[N:11][CH:10]=[N:9][C:8]=32)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516893Potassium BicarbonateHCID 142570878-chloro-5-(4-chlorophenyl)-5H-indeno[1,2-d]pyrimidin-5-ol

Product 1

HCID 142570978-chloro-5-(4-chlorophenyl)-5-fluoro-5H-indeno[1,2-d]pyrimidineYield 75.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 3.0 g of 8-chloro-5-(4-chlorophenyl)-5H-indeno[1,2-d]pyrimidin-5-ol in 50 ml of methylene chloride was cooled to 0° C. under a nitrogen atmosphere. Approximately 2.7 g of diethylaminosulfur trifluoride were added and the reaction was stirred overnight. The mixture was poured into an iced solution of potassium bicarbonate and extracted with ethyl acetate. The organic extract was washed with a sodium bicarbonate solution and a sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo. Crystallization from ethyl acetate/isooctane provided 2.29 g of the desired title product, m.p. 236°-237° C.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with a sodium bicarbonate solution
  4. dry with materiala sodium chloride solution, dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customCrystallization from ethyl acetate/isooctane

Sources & evidence

ORD record
ord-ea165d1e36bf40e283f87d7dc47a953e
Source dataset
uspto-grants-1988_09
Patent number
US04769378

Reaction notes

Loading…