Trichloroacetyl chloride → N-(2-amino-5-trifluoromethyl-3-pyridyl)trichloroacetamide

HRID 257026Notes

Reaction equation

HRID 257026 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[Cl:13][C:14]([Cl:19])([Cl:18])[C:15](Cl)=[O:16]>O1CCCC1>[NH2:1][C:2]1[C:7]([NH:8][C:15](=[O:16])[C:14]([Cl:19])([Cl:18])[Cl:13])=[CH:6][C:5]([C:9]([F:10])([F:12])[F:11])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 6420Trichloroacetyl chlorideHCID 102144255-(Trifluoromethyl)pyridine-2,3-diamine

Product 1

HCID 18987111N-(2-amino-5-trifluoromethyl-3-pyridyl)trichloroacetamideYield 80.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Into 38 ml of dry tetrahydrofuran, 1.5 g of 2,3-diamino-5-trifluoromethylpyridine was dissolved, and a solution mixture comprising 1.54 g of trichloroacetyl chloride and 3.8 ml of dry tetrahydrofuran was dropwise added thereto over a period of 10 minutes. Then, the mixture was reacted at room temperature for 3 hours. After completion of the reaction, precipitated crystals were collected by filtration and washed with tetrahydrofuran to obtain 2.2 g of N-(2-amino-5-trifluoromethyl-3-pyridyl)trichloroacetamide having a melting point of from 210° to 223° C.

Workup

  1. additionwas dropwise added
  2. customThen, the mixture was reacted at room temperature for 3 hours
  3. customAfter completion of the reaction
  4. customprecipitated crystals
  5. filtrationwere collected by filtration
  6. washwashed with tetrahydrofuran

Sources & evidence

ORD record
ord-36fd7649f1874ea583ec2a6c7492c728
Source dataset
uspto-grants-1993_11
Patent number
US05260320

Reaction notes

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