Hydrochloric Acid → methyl 2-methoxy-5-(4H-triazol-1-yl)benzoate

HRID 323449ノート

反応式

HRID 323449 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].CN(C)/[CH:16]=[N:17]/[N:18]=C/N(C)C.[C:24]1(C)C=CC(S(O)(=O)=O)=CC=1.Cl>C1(C)C=CC=CC=1.CO.ClCCl.C(OCC)(=O)C.ClCCl>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:24][CH2:16][N:17]=[N:18]2)=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 89843Methyl 5-amino-o-anisateHCID 9613942N'-((Dimethylamino)methylene)-N,N-dimethylformohydrazonamide

生成物 1

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

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒HCID 21226129Dichloromethane methanol溶媒HCID 21226138Dichloromethane ethylacetate溶媒

実験手順

According to the method of J. Chem. Soc. (C), 1664 (1967), combine methyl 2-methoxy-5-aminobenzoate (2.0 g, 11 mmol), N,N-dimethylformamide azine (1.56 g, 11 mmol), p-toluenesulfonic acid (190 mg) in toluene (25 mL). Fit the reaction vessel with a gas inlet such that the head space of the vessel is swept with argon and scrub the effluent through dilute aqueous hydrochloric acid solution. Heat to reflux. After 20 hours, concentrate the reaction mixture in vacuo to give a residue. Partition the residue between dichloromethane and a saturated aqueous sodium bicarbonate solution. Extract the aqueous layer twice with dichloromethane. Combine the organic layers, dry over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with 70% ethyl acetate/dichloromethane and then 5% methanol/dichloromethane to give a residue. Recrystallize the residue form ethyl acetate/hexane to give methyl 2-methoxy-5-(4H-triazol-1-yl)benzoate: mp; 191-195.5° C.

後処理

  1. customFit the reaction vessel with a gas inlet such that the head space of the vessel is swept with argon
  2. temperatureHeat to reflux
  3. concentrationconcentrate the reaction mixture in vacuo
  4. customto give a residue
  5. customPartition the residue between dichloromethane
  6. extractionExtract the aqueous layer twice with dichloromethane
  7. dry with materialdry over MgSO4
  8. filtrationfilter
  9. customevaporate in vacuo
  10. customto give a residue
  11. customRecrystallize the residue form ethyl acetate/hexane

出典と根拠

ORDレコード
ord-a7c8bd9975bb4a589e096ce3a513b805
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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