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

HRID 1672602Notes

Reaction equation

HRID 1672602 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 was complete (approx. 30 minutes), stirring was continued at RT 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 ethyl 3-oxo-3-{[3-(trifluoromethyl)phenyl]amino}propanoate as a yellow powder (109 g, 99%).

Workup

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

Sources & evidence

ORD record
ord-6a4d9a72c8e04d368523fa80daf0e4b4
Source dataset
uspto-grants-2011_08
Patent number
US07998984B2

Reaction notes

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