Methylamine → HCID 19436763, compound

HRID 1198420Notes

Reaction equation

HRID 1198420 reaction equation
[Cl:1][C:2]1[CH:13]=[C:12]([F:14])[C:11]([C:15]2[C:19]([Cl:20])=[C:18]([C:21]([F:24])([F:23])[F:22])[N:17]([CH3:25])[N:16]=2)=[CH:10][C:3]=1[O:4][CH:5]([CH3:9])[C:6](O)=[O:7].C(Cl)(=O)C(Cl)=O.[CH3:32][NH2:33]>C(Cl)Cl.CN(C=O)C.C1COCC1.O>[Cl:1][C:2]1[CH:13]=[C:12]([F:14])[C:11]([C:15]2[C:19]([Cl:20])=[C:18]([C:21]([F:24])([F:23])[F:22])[N:17]([CH3:25])[N:16]=2)=[CH:10][C:3]=1[O:4][CH:5]([CH3:9])[C:6]([NH:33][CH3:32])=[O:7]

Participants

8

Reactant 3

HCID 6329MethylamineHCID 65578Oxalyl chlorideHCID 19436753HCID 19436753, compound

Product 1

HCID 19436763HCID 19436763, compoundYield 99%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 0.8 g (2.0 mmole) of the product of step A in 100 mL methylene chloride was added 0.5 mL (6.0 mmole) oxalyl chloride over 5 minutes, causing the evolution of gas. When this evolution ceased, one drop of DMF was added and the solution stirred until the gas evolution ceased. The solution was stripped to dryness in vacuo. The residue was dissolved in 10 mL THF and added to a solution of 5 mL 40% aqueous methyl amine and 10 mL THF at 0° C. over 5 minutes. The reaction mixture was allowed to stir for 30 minutes at room temperature. The solution was diluted with 100 mL cold water and extracted with ethyl acetate. The ethyl acetate was washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo. The solid was recrystallized from methylcyclohexane to give 0.83 g (99%) of 2-(2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)- 1H-pyrazol-3-yl)-4-fluorophenoxy)-N-methyl-propanamide as a white solid, mp 134.5°-135.5° C.

Workup

  1. stirringto stir for 30 minutes at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe solid was recrystallized from methylcyclohexane

Sources & evidence

ORD record
ord-3c9c881ebd5e4b36be45fd7dd0e9281a
Source dataset
uspto-grants-1994_01
Patent number
US05281571

Reaction notes

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