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

HRID 1809964

反応式

HRID 1809964 の反応式
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]

参加物

9

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8857Ethyl Acetate溶媒HCID 23503278(Methanesulfinyl)methane--water (1/1)溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-04d8a6fc35784539b2a7b23ce7e955f3
出典データセット
uspto-grants-2013_01
特許番号
US08362050B2

関連ノート

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