1,2-Hydrazinedicarboxaldehyde → methyl 2-methoxy-5-(4H-triazol-1-yl)benzoate

HRID 323450ノート

反応式

HRID 323450 の反応式
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].[CH:14]([NH:16][NH:17]C=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[C:34](=O)(O)[O-].[Na+]>CO.ClCCl.C(OCC)(=O)C.ClCCl>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:34][CH2:14][N:16]=[N:17]2)=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

参加物

7

反応物 4

HCID 123421,2-HydrazinedicarboxaldehydeHCID 14812Phosphorus oxide (P4O10)HCID 89843Methyl 5-amino-o-anisateHCID 516892Sodium Bicarbonate

生成物 1

HCID 22009369methyl 2-methoxy-5-(4H-triazol-1-yl)benzoate

試薬・触媒・溶媒 2

HCID 21226129Dichloromethane methanol溶媒HCID 21226138Dichloromethane ethylacetate溶媒

反応条件

温度
160 °C

実験手順

Alternately, according to the method of J. Med. Chem., 21, 1100 (1978), combine methyl 2-methoxy-5-aminobenzoate (1.8 g, 10 mmol), diformyl hydrazine (0.97 g, 11 mmol), and phosphorous pentoxide (1.84 g, 13 mmol). Heat to 160° C. After 1.5 hours, cool the reaction mixture and add a saturated aqueous solution of sodium bicarbonate. Extract three times with dichloromethane. Dry the combined organic layers over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with 40% ethyl acetate/dichloromethane and then 5% methanol/dichloromethane to give methyl 2-methoxy-5-(4H-triazol-1-yl)benzoate: mp; 179-182° C.

後処理

  1. temperaturecool the reaction mixture
  2. extractionExtract three times with dichloromethane
  3. dry with materialDry the combined organic layers over MgSO4
  4. filtrationfilter
  5. customevaporate in vacuo
  6. customto give a residue

出典と根拠

ORDレコード
ord-51d4e5ada01148b294c4f63a0dbc22fa
出典データセット
uspto-grants-2001_04
特許番号
US06211199B1

反応ノート

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