Pyridine → {4-[4-(5-Bromo-pyridin-2-ylcarbamoyl)-2-nitro-phenylsulfanyl]-phenyl}-carbamic acid 2,2,2-trichloro-ethyl ester

HRID 605324Notes

Reaction equation

HRID 605324 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][N: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:3]=[CH:4][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][N:17]=3)=[CH:11][C:10]=2[N+:25]([O-:27])=[O:26])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 670400914-(4-Amino-phenylsulfanyl)-N-(5-bromo-pyridin-2-yl)-3-nitro-benzamide

Product 1

HCID 67040335{4-[4-(5-Bromo-pyridin-2-ylcarbamoyl)-2-nitro-phenylsulfanyl]-phenyl}-carbamic acid 2,2,2-trichloro-ethyl esterYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of the product of Example 364B (27.5 g, 0.0618 mol) and pyridine (7.73 g, 7.50 mL, 0.0927 mol, 1.5 equiv.) in dichloromethane (500 mL) was stirred at room temperature. To this mixture was added slowly, dropwise 2,2,2-trichloroethyl chloroformate (17.0 g, 10.8 mL, 0.0803 mol, 1.3 equiv.) over 30 minutes. The reaction mixture was stirred at room temperature for 2 hours, during which time the product precipitated as a yellow solid. The mixture was filtered and the filter cake was rinsed with dichloromethane (100 mL) and dried in vacuo to give the title compound (35.3 g, 92%) as a yellow solid.

Workup

  1. additionTo this mixture was added slowly
  2. stirringThe reaction mixture was stirred at room temperature for 2 hours, during which time the product
  3. customprecipitated as a yellow solid
  4. filtrationThe mixture was filtered
  5. washthe filter cake was rinsed with dichloromethane (100 mL)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-8447e5aacf4645fa948a0a178fd92265
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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