Triethylamine → 4-[3-(4-Chlorobenzoylamino)propylthio]pyridine hydrochloride

HRID 2210113

반응식

HRID 2210113 반응식
Cl.Cl.[NH2:3][CH2:4][CH2:5][CH2:6][S:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1.C(N(CC)CC)C.[Cl:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1>C(Cl)Cl>[ClH:21].[Cl:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([NH:3][CH2:4][CH2:5][CH2:6][S:7][C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[O:27])=[CH:24][CH:23]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 190792594-(3-Aminopropylthio)pyridine dihydrochloride

생성물 1

HCID 190791954-[3-(4-Chlorobenzoylamino)propylthio]pyridine hydrochloride수율 118.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 1.00 g (4.15 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.77 ml (19.8 mmol) of triethylamine in 40 ml of methylene chloride was added 0.63 ml (4.96 mmol) of 4-chlorobenzoyl chloride under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was washed with an aqueous saturated sodium bicarbonate solution and water and dried. The solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to obtain the powder which was washed with ether and dried to obtain 1.01 g of the desired compound (free base) (79.3%, pale yellow powder), mp: 95.0°-96.0° C.

후처리

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. washThe reaction mixture was washed with an aqueous saturated sodium bicarbonate solution and water
  4. customdried
  5. distillationThe solvent was distilled off
  6. customThe residue was purified by column chromatography (eluent: ethyl acetate)
  7. customto obtain the powder which
  8. washwas washed with ether
  9. customdried

출처 및 근거

ORD 기록
ord-bd236310fc0d47d09718391e1e869f74
출처 데이터셋
uspto-grants-1995_10
특허 번호
US05457106

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