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

HRID 1360133
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HRID 1360133 반응식
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
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참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2f0ef0ae52fc4963887486c867daabb6
출처 데이터셋
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07879847B2

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