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

HRID 605148Notes

Reaction equation

HRID 605148 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]([S: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:12]=[CH:11][C:10]([S: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:9][CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 67040512{4-[4-(4-Bromo-phenylcarbamoyl)-2-nitro-phenylsulfanyl]-phenyl}-carbamic acid 2,2,2-trichloro-ethyl ester

Product 1

HCID 67040806{4-[2-Amino-4-(4-bromo-phenylcarbamoyl)-phenylsulfanyl]-phenyl}-carbamic acid 2,2,2-trichloro-ethyl esterYield 95%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent2×

Procedure

A solution of the product of Example 100B (1.23 g, 2.0 mmol), iron powder (0.56 g, 10.0 mmol) and ammonium chloride (0.16 g, 3.0) in an ethanol (30 mL), tetrahydrofuran (30 mL), and water (10 mL) solution was heated to reflux for 6 hours. The resultant mixture was diluted with ethanol (50 mL) and filtered through a pad of celite. The filtrate was concentrated under vacuum to a volume of 10 mL, the solution diluted with water (50 mL) and extracted with ethyl acetate (2×50 mL). The combined extracts were dried over sodium sulfate, filtered and concentrated under vacuum to provide the title compound as a yellow powder (1.12 g, 95%).

Workup

  1. temperatureto reflux for 6 hours
  2. filtrationfiltered through a pad of celite
  3. concentrationThe filtrate was concentrated under vacuum to a volume of 10 mL
  4. additionthe solution diluted with water (50 mL)
  5. extractionextracted with ethyl acetate (2×50 mL)
  6. dry with materialThe combined extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-422181b0fc5c429eb0e6e28902a4c19d
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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