Dichloromethane → HCID 14626891, compound

HRID 1085081Notes

Reaction equation

HRID 1085081 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.[NH2:21][C:22]1[CH:23]=[CH:24][C:25]([O:28][CH:29]([C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[C:36]([Cl:41])[CH:35]=2)[C:30]([F:33])([F:32])[F:31])=[N:26][CH:27]=1>C1(C)C=CC=CC=1.C(=O)=O.CCCCCCC>[Cl:41][C:36]1[CH:35]=[C:34]([CH:29]([O:28][C:25]2[CH:24]=[CH:23][C:22]([NH:21][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:27][N:26]=2)[C:30]([F:33])([F:31])[F:32])[CH:39]=[CH:38][C:37]=1[Cl:40]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 874392,6-DifluorobenzamideHCID 13670552HCID 13670552, compound

Product 1

HCID 14626891HCID 14626891, compound

Reagents, catalysts & solvents 3

HCID 280Carbon DioxideSolventHCID 1140TolueneSolvent2×HCID 8900HeptaneSolvent

Procedure

A stirred mixture of 2,6-difluorobenzamide (0.56 g, 0.0036 mole), oxalyl chloride (0.45 g, 0.0036 mole), and methylene chloride (10 ml) in toluene (70 ml) was heated at reflux for three hours. Approximately 10 ml of solvent was removed by distillation under reduced pressure. A solution of 5-amino-2-[1-(3,4-dichlorophenyl)-2,2,2-trifluoroethoxy]pyridine (1.2 g, 0.0036 mole) in toluene (35 ml) was added to the reaction mixture. The resultant solution was stirred at room temperarture for approximately 18 hours. Most of the solvent was evaporated under reduced pressure, leaving a liquid residue. About 150 ml of n-heptane was added to the residue, and the mixture was stirred at room temperature, slowly forming a precipitate. The mixture was cooled in dry ice before collecting the precipitate by filtration. A total of 1.65 g of N-[[[2-[-1-(3,4-dichlorophenyl)2,2,2-trifluoroethoxy]pyridin-5-yl]amino]carbonyl]2,6-difluorobenzamide was collected (mp 171°-172° C.). The nmr and ir spectra were consistent with the proposed structure.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for three hours
  3. customApproximately 10 ml of solvent was removed by distillation under reduced pressure
  4. customMost of the solvent was evaporated under reduced pressure
  5. customleaving a liquid residue
  6. customslowly forming a precipitate
  7. custombefore collecting the precipitate
  8. filtrationby filtration
  9. customA total of 1.65 g of N-[[[2-[-1-(3,4-dichlorophenyl)2,2,2-trifluoroethoxy]pyridin-5-yl]amino]carbonyl]2,6-difluorobenzamide was collected (mp 171°-172° C.)

Sources & evidence

ORD record
ord-61ecba3a73cb4390ab188f13e5e3debb
Source dataset
uspto-grants-1991_04
Patent number
US05008277

Reaction notes

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