Toluene → Benzamide, 3,5-dichloro-2,6-dimethoxy-N-(1-ethyl-2-pyrrolidinylmethyl)-

HRID 224424

반응식

HRID 224424 반응식
S(Cl)(Cl)=O.[Cl:5][C:6]1[C:7]([O:18][CH3:19])=[C:8]([C:12]([O:16][CH3:17])=[C:13]([Cl:15])[CH:14]=1)[C:9]([OH:11])=O.C1(C)C=CC=CC=1.[NH2:27][CH2:28][CH:29]1[CH2:33][CH2:32][CH2:31][N:30]1[CH2:34][CH3:35]>C(OCC)C.O>[CH2:34]([N:30]1[CH2:31][CH2:32][CH2:33][CH:29]1[CH2:28][NH:27][C:9](=[O:11])[C:8]1[C:12]([O:16][CH3:17])=[C:13]([Cl:15])[CH:14]=[C:6]([Cl:5])[C:7]=1[O:18][CH3:19])[CH3:35]

참가 물질

7

반응물 4

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 27747503,5-Dichloro-2,6-dimethoxybenzoic Acid

생성물 1

HCID 54941Benzamide, 3,5-dichloro-2,6-dimethoxy-N-(1-ethyl-2-pyrrolidinylmethyl)-

시약·촉매·용매 2

HCID 962Water용매HCID 3283Diethyl Ether용매

실험 절차

20 ml of thionyl chloride is added to 11.9 g (0.047 mol) of 3,5-dichloro-2,6-dimethoxybenzoic acid. The mixture is heated on a steam bath for 30 minutes. To the solution is added 50 ml of toluene. The solvent and excess thionyl chloride is evaporated at reduced pressure. The residue is dissolved in 50 ml of dry ethyl ether. To the obtained solution is added dropwise while stirring 6.0 g (0.047 mol) of 2-(aminomethyl)-1-ethylpyrrolidine in 50 ml of ethyl ether. After 30 minutes at room temperature 300 ml of water is added while stirring. The water layer is separated and alkalized with sodium hydroxide solution which is added dropwise while stirring and cooling in ice. The precipitate is collected and washed with water. Yield: 9.0 g, m.p. 120°-21° C.

후처리

  1. temperatureThe mixture is heated on a steam bath for 30 minutes
  2. customThe solvent and excess thionyl chloride is evaporated at reduced pressure
  3. dissolutionThe residue is dissolved in 50 ml of dry ethyl ether
  4. additionTo the obtained solution is added dropwise
  5. customThe water layer is separated
  6. additionis added dropwise
  7. stirringwhile stirring
  8. temperaturecooling in ice
  9. customThe precipitate is collected
  10. washwashed with water

출처 및 근거

ORD 기록
ord-b3b738a827e8417e8e72b8888fb1ea24
출처 데이터셋
uspto-grants-1980_11
특허 번호
US04232037

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