Cesium fluoride → 4,4'-Dicyanobenzophenone

HRID 1768634Notes

Reaction equation

HRID 1768634 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1)#[N:2].[F-].[Cs+].C[Si](C)(C)[C:15]1SC=[N:17][CH:16]=1>C1COCC1>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]([C:3]2[CH:10]=[CH:9][C:15]([C:16]#[N:17])=[CH:5][CH:4]=2)=[O:8])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 660424-CyanobenzaldehydeHCID 27608675-Trimethylsilylthiazole

Product 1

HCID 106571914,4'-Dicyanobenzophenone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

15.7 g of 4-cyanobenzaldehyde and 9.1 g of caesium fluoride are added to a solution of 9.4 g of 5-trimethylsilylthiazole in 0.56 l of THF, and the mixture is heated under reflux for 16 hours. The solid material is filtered off and the solvent is concentrated. Column chromatography (SiO2, hexane/ethyl acetate 1:2) yields first (a) 5-(4-cyanobenzoyl)-thiazole [Rf hexane/ethyl acetate 1:2)=0.65], m.p. (after crystallisation from ethyl acetate) 181°-182°; 1H-NMR (CDCl3): δ (ppm)=8.88 and 8 (m,4H), 8.36 (s,1H), 9.14 (s,1H), and then (b)4-(α-hydroxy-5-thiazolylmethyl)-benzonitrile [Rf (hexane/ethyl acetate 1:2)=0.35], m.p. (after crystallisation from toluene) 115°-117°; 1H-NMR (CDCl3): δ (ppm)=3.05 (d,1H), 6.2 (d,1H), 7.58 and 7.7 (m,4H), 7.73 (s,1H), 8.78 (s,1H).

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 16 hours
  3. filtrationThe solid material is filtered off
  4. concentrationthe solvent is concentrated

Sources & evidence

ORD record
ord-7e570e3601004d7ab5ef7d5f4d8b6fb3
Source dataset
uspto-grants-1995_01
Patent number
US05378721

Reaction notes

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