Pyridine → HCID 67041134, compound

HRID 884020Notes

Reaction equation

HRID 884020 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=2[N+:19]([O-:21])=[O:20])=[CH:4][C:3]=1[F:22].N1C=CC=CC=1.Cl[C:30]([O:32][CH2:33][C:34]([Cl:37])([Cl:36])[Cl:35])=[O:31]>C(Cl)Cl>[F:22][C:3]1[CH:4]=[C:5]([S:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=2[N+:19]([O-:21])=[O:20])[CH:6]=[CH:7][C:2]=1[NH:1][C:30]([O:32][CH2:33][C:34]([Cl:37])([Cl:36])[Cl:35])=[O:31]

Participants

5

Reactant 3

HCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 67040417Benzoic acid, 4-[(4-amino-3-fluorophenyl)thio]-3-nitro-, methyl ester

Product 1

HCID 67041134HCID 67041134, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

The product of Example 96B (2.0 g, 6.2 mmol) and pyridine (0.55 mL, 6.8 mmol) in CH2Cl2 (20 mL) was reacted with 2,2,2-trichloroethyl chloroformate (0.92 mL, 6.5 mmol) dropwise at 5° C. The mixture was stirred at 5° C. for 30 minutes and concentrated. The residue was diluted with water (50 mL). The resulting crystals were collected by filtration, washed with water and i-Pr2O, and dried at room temperature in vacuum overnight to give the title compound as pale yellow crystals (2.9 g, 93%).

Workup

  1. concentrationconcentrated
  2. additionThe residue was diluted with water (50 mL)
  3. filtrationThe resulting crystals were collected by filtration
  4. washwashed with water and i-Pr2O
  5. customdried at room temperature in vacuum overnight

Sources & evidence

ORD record
ord-8ce8616f1c8141da97a59eba48903609
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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