Sodium hydride → 2-[4-(4-Chlorophenyl)-1-piperazinyl]-ethyl 3-(8-trifluoromethyl 4-quinolylamino)-2-thiophene-carboxylate

HRID 838948노트

반응식

HRID 838948 반응식
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[C:8]2[NH:13][C:14]1[CH:18]=[CH:17][S:16][C:15]=1[C:19]([O:21][CH3:22])=[O:20].[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]2[CH2:37][CH2:36][N:35]([CH2:38]CO)[CH2:34][CH2:33]2)=[CH:28][CH:27]=1.[H-].[Na+]>C1(C)C=CC=CC=1>[F:24][C:2]([F:1])([F:23])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[C:8]2[NH:13][C:14]1[CH:18]=[CH:17][S:16][C:15]=1[C:19]([O:21][CH2:22][CH2:38][N:35]1[CH2:34][CH2:33][N:32]([C:29]2[CH:30]=[CH:31][C:26]([Cl:25])=[CH:27][CH:28]=2)[CH2:37][CH2:36]1)=[O:20]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 2582112-[4-(4-Chlorophenyl)piperazin-1-yl]ethanolHCID 15916787Methyl 3-(8-trifluoromethyl-4-quinolylamino)-2-thiophene-carboxylate

생성물 1

HCID 203254662-[4-(4-Chlorophenyl)-1-piperazinyl]-ethyl 3-(8-trifluoromethyl 4-quinolylamino)-2-thiophene-carboxylate수율 76.7%

시약·촉매·용매 1

HCID 1140Toluene용매2회

반응 조건

온도
60 °C

실험 절차

A mixture of 7.04 g of methyl 3-(8-trifluoromethyl-4-quinolylamino)-2-thiophene-carboxylate, 5.5 g of 4-(4-chlorophenyl)-1-piperazine ethanol and 50 ml of anhydrous toluene was refluxed for an hour while passing condensed toluene through a column filled with siliporite and after cooling the mixture to 60° C, 150 ml of sodium hydride were added. The mixture was refluxed with stirring for 16 hours and the toluene was distilled. The residue was extracted with methylene chloride, was washed and dried. The product was crystallized from 95% ethanol, iced and vacuum filtered. The precipitate was washed with ethanol and dried to obtain 8.6 g of 2-[4-(4-chlorophenyl)-1-piperazinyl]-ethyl 3-(8-trifluoromethyl 4-quinolylamino)-2-thiophene-carboxylate melting at 155° C.

후처리

  1. temperaturewas refluxed for an hour
  2. additionfilled with siliporite and
  3. temperatureThe mixture was refluxed
  4. distillationthe toluene was distilled
  5. extractionThe residue was extracted with methylene chloride
  6. washwas washed
  7. customdried
  8. customThe product was crystallized from 95% ethanol
  9. filtrationiced and vacuum filtered
  10. washThe precipitate was washed with ethanol
  11. customdried

출처 및 근거

ORD 기록
ord-cdb6d4f942434e97a4b5e05c05f13702
출처 데이터셋
uspto-grants-1978_06
특허 번호
US04093724

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