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

HRID 605320Notes

Reaction equation

HRID 605320 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-51f3af755adb470e865fbeb00f653ebb
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

Loading…