Cesium carbonate → 4-(5,6-Dihydro-8H-imidazo[5,1-c][1,4]oxazin-5-yl)benzonitrile

HRID 1360133Notes

Reaction equation

HRID 1360133 reaction equation
CS(O[CH:6]([C:34]1[CH:39]=[CH:38][C:37]([C:40]#[N:41])=[CH:36][CH:35]=1)[CH2:7][O:8][CH2:9][C:10]1[N:11]=[CH:12][N:13](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:14]=1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.O>[CH:14]1[N:13]=[CH:12][N:11]2[CH:6]([C:34]3[CH:39]=[CH:38][C:37]([C:40]#[N:41])=[CH:36][CH:35]=3)[CH2:7][O:8][CH2:9][C:10]=12

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 866329521-(4-cyanophenyl)-2-(1-trityl-1H-imidazol-4-ylmethoxy)ethyl methanesulphonate

Product 1

HCID 167527064-(5,6-Dihydro-8H-imidazo[5,1-c][1,4]oxazin-5-yl)benzonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 1.00 mmol of 1-(4-cyanophenyl)-2-(1-trityl-1H-imidazol-4-ylmethoxy)ethyl methanesulphonate in 5 ml of N,N-dimethylformamide is mixed with 2.50 mmol of caesium carbonate and heated at 80° C. for 6 hours. The reaction mixture is cooled to room temperature, diluted with water and extracted with ethyl acetate (2×). The combined organic phases are dried with sodium sulphate and evaporated. The title compound is obtained from the residue as yellowish crystals by flash chromatography (SiO2 60F). Rf=0.61 (dichloromethane-methanol-25% aqueous ammonia solution 200:10:1); Rt=3.54 (gradient II).

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. extractionextracted with ethyl acetate (2×)
  3. dry with materialThe combined organic phases are dried with sodium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-2f0ef0ae52fc4963887486c867daabb6
Source dataset
uspto-grants-2011_02
Patent number
US07879847B2

Reaction notes

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