Diphenylacetonitrile → Ammonia

HRID 450924노트

반응식

HRID 450924 반응식
CC(C)([O-])C.[K+].[CH3:7][C:8]1([CH3:23])[CH2:13][CH2:12]OS(=O)(=O)[N:9]1C(OC(C)(C)C)=O.[C:24]1([CH:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:31]#[N:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C)C=O>[NH3:9].[NH2:9][C:8]([CH3:7])([CH3:23])[CH2:13][CH2:12][C:30]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:31]#[N:32]

참가 물질

6

반응물 3

HCID 6837DiphenylacetonitrileHCID 23665647Potassium tert-butoxideHCID 59383129HCID 59383129, 화합물

생성물 2

HCID 222AmmoniaHCID 54757654HCID 54757654, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Potassium tert-butoxide (203 mg, 1.81 mmol) and tert-butyl 4,4-dimethyl-1,2,3-oxathiazinane-3-carboxylate 2,2-dioxide [(400 mg, 1.51 mmol), WO2003037327, p 83] were added to a solution of diphenylacetonitrile (349 mg, 1.81 mmol) in N,N-dimethylformamide (5 mL) and the mixture was stirred for 18 hours at room temperature. The reaction mixture was then concentrated in vacuo and the residue was treated with hydrochloric acid (4M in dioxane, 10 mL) and heated at 40° C. for 2.5 hours. The reaction mixture was concentrated in vacuo and the residue was basified with saturated sodium hydrogen carbonate solution and extracted with ethyl acetate (2×30 mL). The combined organic solution was dried over magnesium sulfate, concentrated in vacuo and the residue was purified by column chromatography on silica gel, eluting with dichloromethane:methanol:0.88 ammonia, 90:10:1, to afford the title compound as a colourless oil in 77% yield, 324 mg.

후처리

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. additionthe residue was treated with hydrochloric acid (4M in dioxane, 10 mL)
  3. temperatureheated at 40° C. for 2.5 hours
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. extractionextracted with ethyl acetate (2×30 mL)
  6. dry with materialThe combined organic solution was dried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customthe residue was purified by column chromatography on silica gel
  9. washeluting with dichloromethane

출처 및 근거

ORD 기록
ord-b2962aa7c1de4afdb6540c4477d3769d
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486992B2

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