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

HRID 605295Notes

Reaction equation

HRID 605295 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 the product from Example 268A (4.2 g, 9.8 mmol) dissolved in dichloromethane (100 mL) was added pyridine (1.62 mL, 20 mmol) followed by the dropwise addition of 2,2,2-trichloroethyl chloroformate (2.29 g, 10.8 mmol). The resultant solution was stirred for 4 hours and then concentrated under vacuum. The mixture was then poured into water (200 mL), the pH of the solution adjusted to 5 with 1N aqueous hydrochloric acid, the resultant solution stirred for 30 minutes and the resultant solid collected and dried to provide the title compound (6.0 g, 100%).

Workup

  1. concentrationconcentrated under vacuum
  2. additionThe mixture was then poured into water (200 mL)
  3. customthe resultant solid collected
  4. customdried

Sources & evidence

ORD record
ord-f83bf93cce5f4e07985585efe10d8cec
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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