Dichloromethane → HCID 14100468, compound

HRID 648986Notes

Reaction equation

HRID 648986 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([NH2:6])=[O:5].C(Cl)(=O)[C:13](Cl)=[O:14].C(Cl)Cl.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:43])([F:42])[C:29]([F:41])([F:40])[O:30][C:31]2[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][C:32]=2[O:38][CH3:39])=[CH:24][CH:23]=1>C1(C)C=CC=CC=1.CCCCCCC>[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]([F:42])([F:43])[C:29]([F:40])([F:41])[O:30][C:31]2[CH:37]=[CH:36][C:34]([NH:35][C:13]([NH:6][C:4](=[O:5])[C:3]3[C:2]([F:1])=[CH:10][CH:9]=[CH:8][C:7]=3[F:11])=[O:14])=[CH:33][C:32]=2[O:38][CH3:39])=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 874392,6-DifluorobenzamideHCID 14100467HCID 14100467, compound

Product 1

HCID 14100468HCID 14100468, compoundYield 93.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8900HeptaneSolvent

Procedure

A stirred mixture of 2,6-difluorobenzamide (0.37 g, 0.027 mole), oxalyl chloride (0.33 g, 0.0026 mole) and methylene chloride (3.0 mL) in toluene (80 mL) was heated at reflux for three hours. Approximately 40 mL of solvent was removed by distillation under reduced pressure. A solution of 4-[2-(4-chlorophenyl)-1,1,2,2-tetrafluoroethoxy]-3-methoxyaniline (0.83 g, 0.0024 mole) in toluene (40 mL) was added to the reaction mixture. The resultant solution was stirred at room temperature for approximately 18 hours. About 40 mL of the solvent was removed by evaporation under reduced pressure, leaving a liquid residue. Approximately 100 mL of n-heptane was added to the residue, and the mixture was stirred at room temperature, slowly forming a precipitate. This solid was collected by filtration to yield 1.2 g of N-[[[4-[2-(4-chlorophenyl)-1,1,2,2-tetrafluoroethoxy]-3-methoxyphenyl]amino]carbonyl]-2,6-difluorobenzamide, m.p. 133°-134.5° C., Compound 10 of Table 1.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for three hours
  3. customApproximately 40 mL of solvent was removed by distillation under reduced pressure
  4. customAbout 40 mL of the solvent was removed by evaporation under reduced pressure
  5. customleaving a liquid residue
  6. customslowly forming a precipitate
  7. filtrationThis solid was collected by filtration

Sources & evidence

ORD record
ord-58adad3608da45439da06b17be4e719c
Source dataset
uspto-grants-1988_04
Patent number
US04737509

Reaction notes

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