Ammonium Chloride → {4-[2-Amino-4-(4-bromo-phenylcarbamoyl)-phenoxy]-phenyl}-carbamic acid 2,2,2-trichloro-ethyl ester

HRID 605320노트

반응식

HRID 605320 반응식
[Cl:1][C:2]([Cl:35])([Cl:34])[CH2:3][O:4][C:5](=[O:33])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:29])[NH:21][C:22]3[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=3)=[CH:16][C:15]=2[N+:30]([O-])=O)=[CH:9][CH:8]=1.[Cl-].[NH4+]>O1CCCC1.C(O)C.O.[Fe]>[Cl:35][C:2]([Cl:1])([Cl:34])[CH2:3][O:4][C:5](=[O:33])[NH:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:29])[NH:21][C:22]3[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=3)=[CH:16][C:15]=2[NH2:30])=[CH:11][CH:12]=1

참가 물질

5

반응물 2

HCID 25517Ammonium ChlorideHCID 67040283{4-[4-(4-Bromo-phenylcarbamoyl)-2-nitro-phenoxy]-phenyl}-carbamic acid 2,2,2-trichloro-ethyl ester

생성물 1

HCID 67040452{4-[2-Amino-4-(4-bromo-phenylcarbamoyl)-phenoxy]-phenyl}-carbamic acid 2,2,2-trichloro-ethyl ester수율 83%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 18504229Ethanol tetrahydrofuran water용매

실험 절차

A mixture of the product of Example 361D (6.0 g, 10.0 mmol), iron powder (2.8 g, 50 mmol, 5 equiv, from Acros, electrolytically reduced, reagent, powder), and ammonium chloride (0.81 g, 15.0 mmol, 1.5 equiv) in tetrahydrofuran/ethanol/water (60/60/20 mL) was heated under reflux for 5 hours. The reaction mixture was cooled to room temperature and filtered through Celite, rinsing the Celite pad with 50 mL of ethanol. The resulting filtrate was evaporated under reduced pressure and the residue was partitioned between ethyl acetate (100 mL) and water (100 mL). The aqueous phase was extracted with ethyl acetate (2×100 mL). The combined organic phases were washed with brine (50 mL), dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure to give the title compound (4.71 g, 83%) as a tan solid.

후처리

  1. temperatureunder reflux for 5 hours
  2. filtrationfiltered through Celite
  3. washrinsing the Celite pad with 50 mL of ethanol
  4. customThe resulting filtrate was evaporated under reduced pressure
  5. customthe residue was partitioned between ethyl acetate (100 mL) and water (100 mL)
  6. extractionThe aqueous phase was extracted with ethyl acetate (2×100 mL)
  7. washThe combined organic phases were washed with brine (50 mL)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-51f3af755adb470e865fbeb00f653ebb
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910595B2

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