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

HRID 605296Notes

Reaction equation

HRID 605296 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.O>C(O)C.[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

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 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 42%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

The product from Example 268B (6.0 g, 10 mmol), iron powder (2.8 g, 50 mmol) and ammonium chloride (0.81 g, 15 mmol) in a mixture of ethanol (60 mL), tetrahydrofuran (60 mL), and water (20 mL) was heated under reflux for 5 hours and then cooled to room temperature. The reaction mixture was filtered through Celite and the filter pad was rinsed with ethanol (100 mL). The filtrate was evaporated under reduced pressure to leave a residue which was triturated with hexanes/ethyl acetate 4/1 to provide the title product (2.39 g, 42%) as a tan solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. filtrationThe reaction mixture was filtered through Celite
  4. washthe filter pad was rinsed with ethanol (100 mL)
  5. customThe filtrate was evaporated under reduced pressure
  6. customto leave a residue which
  7. customwas triturated with hexanes/ethyl acetate 4/1

Sources & evidence

ORD record
ord-48e664271e1e422189aade1c72221acf
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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