Pyridine → {4-[4-(4-Bromo-phenylcarbamoyl)-2-nitro-phenoxy]-phenyl}-carbamic acid 2,2,2-trichloro-ethyl ester

HRID 605319Notes

Reaction equation

HRID 605319 reaction equation
[NH2:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[CH:22]=[CH:21][C:10]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=3)=[O:12])=[CH:9][C:8]=2[N+:23]([O-:25])=[O:24])=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:35]([O:37][CH2:38][C:39]([Cl:42])([Cl:41])[Cl:40])=[O:36]>ClCCl>[Cl:40][C:39]([Cl:42])([Cl:41])[CH2:38][O:37][C:35](=[O:36])[NH:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[CH:22]=[CH:21][C:10]([C:11](=[O:12])[NH:13][C:14]3[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=3)=[CH:9][C:8]=2[N+:23]([O-:25])=[O:24])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 670405064-(4-Amino-phenoxy)-N-(4-bromo-phenyl)-3-nitro-benzamide

Product 1

HCID 67040283{4-[4-(4-Bromo-phenylcarbamoyl)-2-nitro-phenoxy]-phenyl}-carbamic acid 2,2,2-trichloro-ethyl esterYield 101.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of the product of Example 361C (4.2 g, 9.8 mmol) and pyridine (1.6 g, 1.62 mL, 20 mmol) in dichloromethane (100 mL) was added dropwise 2,2,2-trichloroethyl chloroformate (2.29 g, 10.8 mmol) over 30 minutes. The reaction mixture was stirred for 4 hours, concentrated and the residue was poured into 200 mL of water adjusting the pH to 5 with 1 M HCl. The mixture was stirred for 30 minutes, filtered, and the collected solid was dried in vacuo to give the title compound (6.0 g, 98%).

Workup

  1. concentrationconcentrated
  2. additionthe residue was poured into 200 mL of water adjusting the pH to 5 with 1 M HCl
  3. stirringThe mixture was stirred for 30 minutes
  4. filtrationfiltered
  5. customthe collected solid was dried in vacuo

Sources & evidence

ORD record
ord-da98db06b2aa4dceac55c13490fb82ce
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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