3-(Trifluoromethyl)aniline → Ethyl 3-oxo-3-{[3-(trifluoromethyl)phenyl]amino}propanoate

HRID 559785Notes

Reaction equation

HRID 559785 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].C(N(CC)CC)C.Cl[C:20](=[O:27])[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>CC(C)=O>[O:27]=[C:20]([NH:6][C:5]1[CH:7]=[CH:8][CH:9]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=1)[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

5

Reactant 3

HCID 73753-(Trifluoromethyl)anilineHCID 8471TriethylamineHCID 118931Ethyl 3-chloro-3-oxopropionate

Product 1

HCID 3651864Ethyl 3-oxo-3-{[3-(trifluoromethyl)phenyl]amino}propanoateYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To an ice-cooled solution of 3-(trifluoromethyl)aniline (64.5 g, 0.40 mol) and triethylamine (60 ml) in acetone (700 ml) was added dropwise, ethyl 3-chloro-3-oxopropanoate (63.6 g, 0.42 mol) in acetone (50 ml). After the addition (approx. 30 minutes) stirring was continued at room temperature overnight. The solvents were removed and water (1200 ml) was added. The resulting precipitate was filtered off, thoroughly washed twice with water and then dried to afford the title compound as yellow powder (109 g, 99%).

Workup

  1. additionwas added dropwise
  2. additionAfter the addition (approx. 30 minutes)
  3. customThe solvents were removed
  4. additionwater (1200 ml) was added
  5. filtrationThe resulting precipitate was filtered off
  6. washthoroughly washed twice with water
  7. customdried

Sources & evidence

ORD record
ord-c6fa927967324d328a84e49b75ed1b6f
Source dataset
uspto-grants-2011_11
Patent number
US08063073B2

Reaction notes

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