N,N'-Dimethylethylenediamine → ethyl 3-[4-(4-ethylphenyl)-1H-1,2,3-triazol-1-yl]benzoate

HRID 1809964

반응식

HRID 1809964 반응식
I[C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[N-:13]=[N+:14]=[N-:15].[Na+].[CH2:17]([C:19]1[CH:24]=[CH:23][C:22]([C:25]#[CH:26])=[CH:21][CH:20]=1)[CH3:18].CNCCNC.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>[Cu]I.C(OCC)(=O)C.CS(C)=O.O>[CH2:25]([C:22]1[CH:23]=[CH:24][C:19]([C:17]2[N:13]=[N:14][N:15]([C:2]3[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=3)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:18]=2)=[CH:20][CH:21]=1)[CH3:26]

참가 물질

9

반응물 5

HCID 8070N,N'-DimethylethylenediamineHCID 33557Sodium AzideHCID 1424251-Ethyl-4-ethynylbenzeneHCID 143542Ethyl 3-iodobenzoateHCID 23667548Sodium Ascorbate

생성물 1

HCID 67030215ethyl 3-[4-(4-ethylphenyl)-1H-1,2,3-triazol-1-yl]benzoate

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8857Ethyl Acetate용매HCID 23503278(Methanesulfinyl)methane--water (1/1)용매

실험 절차

A mixture of ethyl 3-iodobenzoate (4-1) (138 mg, 0.5 mmol), sodium azide (34 mg, 0.52 mmol), 1-ethyl-4-ethynylbenzene (4-2) (65 mg, 0.5 mmol), CuI (10 mg), MeNHCH2CH2NHMe (11 μL), sodium ascorbate (10 mg), DMSO-H2O (v/v 5:1, 1.5 mL) is stirred at room temperature for 2 hours. The reaction mixture is then poured into ethyl acetate (50 mL), washed with water (10 mL) and brine (10 mL), dried over Na2SO4, filtered and evaporated. The residue is purified on silica gel (0-33% ethyl acetate in hexane) to give ethyl 3-[4-(4-ethylphenyl)-1H-1,2,3-triazol-1-yl]benzoate as a white solid.

후처리

  1. washwashed with water (10 mL) and brine (10 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue is purified on silica gel (0-33% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-04d8a6fc35784539b2a7b23ce7e955f3
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362050B2

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