Hydrochloric Acid → N-[6-(3-aminophenoxy)-1,3-benzothiazol-2-yl]cyclopropanecarboxamide

HRID 2190363

반응식

HRID 2190363 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][CH:25]=1)[O:7][C:8]1[CH:22]=[CH:21][C:11]2[N:12]=[C:13]([NH:15][C:16]([CH:18]3[CH2:20][CH2:19]3)=[O:17])[S:14][C:10]=2[CH:9]=1)([O-])=O.Cl>C(O)C.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][CH:25]=1)[O:7][C:8]1[CH:22]=[CH:21][C:11]2[N:12]=[C:13]([NH:15][C:16]([CH:18]3[CH2:20][CH2:19]3)=[O:17])[S:14][C:10]=2[CH:9]=1

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 57749256N-[6-(3-nitrophenoxy)-1,3-benzothiazol-2-yl]cyclopropanecarboxamide

생성물 1

HCID 86655349N-[6-(3-aminophenoxy)-1,3-benzothiazol-2-yl]cyclopropanecarboxamide수율 108.5%

시약·촉매·용매 2

HCID 23925Iron촉매2회HCID 702Ethanol용매

실험 절차

To a solution of N-[6-(3-nitrophenoxy)-1,3-benzothiazol-2-yl]cyclopropanecarboxamide (840 mg, 2.36 mmol) in ethanol (100 mL) was added iron powder (11.9 g, 212 mmol) with heating under reflux. The obtained suspension was vigorously stirred, and 6N hydrochloric acid (50 mL) was slowly added dropwise. The reaction mixture was refluxed for 2 hr with vigorous stirring, and excess iron powder was filtered off through celite. The filtrate was concentrated to about 50 mL, and the residue was diluted with ethyl acetate (250 mL), washed with 1N aqueous sodium hydroxide solution (100 mLx2) and saturated brine (100 mL), successively, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated to give the title compound (833 mg) as a pale-yellow solid.

후처리

  1. temperaturewith heating
  2. temperatureunder reflux
  3. filtrationwas filtered off through celite
  4. concentrationThe filtrate was concentrated to about 50 mL
  5. additionthe residue was diluted with ethyl acetate (250 mL)
  6. washwashed with 1N aqueous sodium hydroxide solution (100 mLx2) and saturated brine (100 mL)
  7. dry with materialsuccessively, and dried over anhydrous magnesium sulfate
  8. filtrationThe insoluble material was filtered off
  9. concentrationthe filtrate was concentrated

출처 및 근거

ORD 기록
ord-dfc0d77cedde44388ed4247e39f53fbf
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324395B2

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