Triethylamine → Ethyl 2-[4-chloro-2-(trifluoromethyl)anilino]-2-oxoacetate

HRID 1461257Notes

Reaction equation

HRID 1461257 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].C(N(CC)CC)C.[C:20](Cl)([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:21].[Cl-].C([NH+](CC)CC)C>O1CCCC1>[C:20]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]([F:12])([F:10])[F:11])([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:21]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 67961Benzenamine, 4-chloro-2-(trifluoromethyl)-HCID 12698378Triethylazanium chloride

Product 1

HCID 4550962Ethyl 2-[4-chloro-2-(trifluoromethyl)anilino]-2-oxoacetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A mixture of 2-amino-5-chlorobenzotrifluoride (14.4 ml, 0.1 mol) and triethylamine (14.0 ml, 0.1 mol) was dissolved in dry tetrahydrofuran, THF (250 ml). To this solution was added with stirring a solution of ethoxalyl chloride in THF (50 ml). After completion of the addition (30 min.) the mixture was stirred at ambient temperature for 3 h, whereafter the precipitated triethylammonium chloride was filtered off, and the filtrate was evaporated in vacuo. This left the crude title compound (24 g) as pale crystals. M.p. 55°-58° C.

Workup

  1. additionTo this solution was added
  2. additionAfter completion of the addition (30 min.) the mixture
  3. filtrationwas filtered off
  4. customthe filtrate was evaporated in vacuo
  5. waitThis left the crude title compound (24 g) as pale crystals

Sources & evidence

ORD record
ord-40569efa74154781bbc2e040ea04ff3a
Source dataset
uspto-grants-1991_12
Patent number
US05075304

Reaction notes

Loading…