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

HRID 605147Notes

Reaction equation

HRID 605147 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:24]=[CH:23][C:12]([C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=3)=[O:14])=[CH:11][C:10]=2[N+:25]([O-:27])=[O:26])=[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:7]=[CH:6][C:5]([S:8][C:9]2[CH:24]=[CH:23][C:12]([C:13](=[O:14])[NH:15][C:16]3[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=3)=[CH:11][C:10]=2[N+:25]([O-:27])=[O:26])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 670408504-(4-Amino-phenylsulfanyl)-N-(4-bromo-phenyl)-3-nitro-benzamide

Product 1

HCID 67040512{4-[4-(4-Bromo-phenylcarbamoyl)-2-nitro-phenylsulfanyl]-phenyl}-carbamic acid 2,2,2-trichloro-ethyl esterYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a slurry of the product of Example 100A (3.6 g, 8.1 mmol) in dichloromethane (100 mL) and pyridine (1.3 g, 16.2 mmol) was added 2,2,2-Trichloroethyl chloroformate (2.16 g, 10.2 mmol). The solution was stirred for 16 hours, washed with water, brine, dried over sodium sulfate and concentrated under vacuum. The resulting residue was triturated in 9:1 hexane/ethyl acetate to give the title compound as an orange powder (4.15 g, 83%).

Workup

  1. washwashed with water, brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe resulting residue was triturated in 9:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-19776567343340e4b5183ba66ea16f5c
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

Loading…