Triethylamine → HCID 13657069, compound

HRID 979325

Reaction equation

HRID 979325 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:14]([O-:16])=[O:15])=[C:9]([CH:13]=1)[C:10](Cl)=[O:11].[C:25]([O:35][CH2:36][CH3:37])(=[O:34])[CH:26]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[OH:27].C(N(CC)CC)C>CC(C)=O.O>[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:14]([O-:16])=[O:15])=[C:9]([CH:13]=1)[C:10]([O:27][CH:26]([C:25]([O:35][CH2:36][CH3:37])=[O:34])[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:11]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 24197Diethyl malateHCID 30177655-(2-Chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoyl chloride

Product 1

HCID 13657069HCID 13657069, compoundYield 66.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent3×HCID 962WaterSolvent

Procedure

To a stirred solution of 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoyl chloride (3.8 g, 0.01 mole) in acetone (10 ml) was successively added diethyl DL malate (1.9 g, 0.01 mole) in acetone (10 ml) and triethylamine (1.01 g, 0.01 mole) in acetone (5 ml). A white precipitate quickly formed. The reaction was heated to reflux for 24 hours. Upon cooling, the reaction was poured in water (75 ml) and extracted twice with methylene chloride (25 ml @). The combined organic extracts were successively washed with 5% sodium hydroxide and brine solutions. The dried solution was stripped of solvent to give 3.56 g of an amber oil.

Workup

  1. customA white precipitate quickly formed
  2. temperatureThe reaction was heated
  3. temperatureto reflux for 24 hours
  4. temperatureUpon cooling
  5. extractionextracted twice with methylene chloride (25 ml @)
  6. washThe combined organic extracts were successively washed with 5% sodium hydroxide and brine solutions

Sources & evidence

ORD record
ord-c3b3c7d9e0284cfe931dcb2aa93c815f
Source dataset
uspto-grants-1987_05
Patent number
US04667052

Linked notes

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