Ethyl Acetate → (+/-)-1,1-dimethyl-1a,3,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carbonitrile

HRID 1432803노트

반응식

HRID 1432803 반응식
[CH3:1][C:2]1([CH3:14])[CH:4]2[CH2:5][C:6]3[C:10]([CH:3]12)=[N:9][NH:8][C:7]=3[C:11]([NH2:13])=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(OCC)(=O)C>C1COCC1>[CH3:1][C:2]1([CH3:14])[CH:4]2[CH2:5][C:6]3[C:10]([CH:3]12)=[N:9][NH:8][C:7]=3[C:11]#[N:13]

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 9845Trifluoroacetic anhydrideHCID 178421816HCID 178421816, 화합물

생성물 1

HCID 178421815(+/-)-1,1-dimethyl-1a,3,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carbonitrile

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

(±)-1,1-Dimethyl-1a,3,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acid amide (0.532 g, 2.79 mmol) was taken up in THF (150 mL) and trifluoroacetic anhydride (0.936 g, 4.46 mmol) added. The resulting solution was stirred at room temperature under argon for 1 hour. Ethyl acetate (50 mL) was added and solvent removed under reduced pressure. The resulting pale yellow oil was taken up in DCM (100 mL), washed with saturated aqueous sodium bicarbonate solution (40 mL) and solvent removed under reduced pressure. The resulting white solid was taken up as a suspension in DCM (20 mL) and filtered to give (±)-1,1-dimethyl-1a,3,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carbonitrile as an off-white solid. m/z (ES+): 174 [M+H]+

후처리

  1. customsolvent removed under reduced pressure
  2. washwashed with saturated aqueous sodium bicarbonate solution (40 mL) and solvent
  3. customremoved under reduced pressure
  4. filtrationfiltered

출처 및 근거

ORD 기록
ord-06a73ddfeaa24553acba18095d3489af
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612106B2

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