Homoveratrylamine → N-[2-(3,4-dimethoxyphenyl)ethyl]-4-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-butyramide

HRID 35250

반응식

HRID 35250 반응식
[CH3:1][N:2]1[C:6]([CH2:7][CH2:8][CH2:9][C:10](O)=[S:11])=[N:5][N:4]=[N:3]1.C1CCN2C(=NCCC2)CC1.ClC(OCC(C)C)=O.[CH3:32][O:33][C:34]1[CH:35]=[C:36]([CH2:42][CH2:43][NH2:44])[CH:37]=[CH:38][C:39]=1[O:40][CH3:41]>O1CCCC1>[CH3:32][O:33][C:34]1[CH:35]=[C:36]([CH2:42][CH2:43][NH:44][C:10](=[S:11])[CH2:9][CH2:8][CH2:7][C:6]2[N:2]([CH3:1])[N:3]=[N:4][N:5]=2)[CH:37]=[CH:38][C:39]=1[O:40][CH3:41]

참가 물질

6

반응물 4

HCID 8421HomoveratrylamineHCID 62365Isobutyl chloroformateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178482013HCID 178482013, 화합물

생성물 1

HCID 54050218N-[2-(3,4-dimethoxyphenyl)ethyl]-4-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-butyramide수율 41%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

4-(1-Methyl-1,2,3,4-tetrazol-5-yl)thio-butyric acid (45 mmole) is dissolved in tetrahydrofuran (50 ml), and thereto is added DBU (50 mmole). To the mixture is added dropwise with stirring isobutyl chloroformate (50 mmole) under ice-cooling and the mixture is stirred at room temperature for 30 minutes. To the mixture is added dropwise 2-(3,4-dimethoxyphenyl)ethylamine (54 mmole) and the mixture is further stirred at room temperature for 2 hours. After the solvent is distilled off under reduced pressure, the resulting residue is extracted with chloroform. The chloroform layer is washed with 5% aqueous hydrochloric acid, an aqueous saturated sodium hydrogen carbonate solution and an aqueous saturated sodium chloride solution and dried over anhydrous sodium sulfate. After distilling off chloroform, the residue is subjected to column chromatography (Wakogel C-200, eluting agent, chloroform) to isolate N-[2-(3,4-dimethoxyphenyl)ethyl]-4-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-butyramide (yield: 41%) which is recrystallized from hexane-chloroform, colorless flaks, m.p. 70.5°-71.5° C.

후처리

  1. temperaturecooling
  2. stirringthe mixture is further stirred at room temperature for 2 hours
  3. distillationAfter the solvent is distilled off under reduced pressure
  4. extractionthe resulting residue is extracted with chloroform
  5. washThe chloroform layer is washed with 5% aqueous hydrochloric acid
  6. dry with materialan aqueous saturated sodium hydrogen carbonate solution and an aqueous saturated sodium chloride solution and dried over anhydrous sodium sulfate
  7. distillationAfter distilling off chloroform
  8. washthe residue is subjected to column chromatography (Wakogel C-200, eluting agent, chloroform)

출처 및 근거

ORD 기록
ord-4a703fea81f6423fa60176b3220e22fe
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04766120

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