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

HRID 323450노트

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HRID 323450 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 21226129Dichloromethane methanol용매HCID 21226138Dichloromethane ethylacetate용매

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온도
160 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-51d4e5ada01148b294c4f63a0dbc22fa
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211199B1

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