Triethylamine → HCID 13187387, compound

HRID 434589

Reaction equation

HRID 434589 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].C(N(CC)CC)C.[Cl:14][C:15]1[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[CH:30][C:16]=1[O:17][C:18]1[CH:19]=[C:20]([C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=1)[C:21](Cl)=[O:22]>C1(C)C=CC=CC=1>[Cl:14][C:15]1[CH:33]=[C:32]([C:34]([F:35])([F:37])[F:36])[CH:31]=[CH:30][C:16]=1[O:17][C:18]1[CH:19]=[C:20]([C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=1)[C:21]([N:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6])=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 120252-PyrrolidoneHCID 30177655-(2-Chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoyl chloride

Product 1

HCID 13187387HCID 13187387, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Pyrrolidin-2-one (7.60 grams; 0.02 mol), triethylamine (2.0 grams; 0.02 mol) and toluene (50 mol) were placed in a three-necked, glass reaction flask equipped with stirrer, thermometer, addition funnel and drying tube. 3-(2-Chloro-4-trifluoromethylphenoxy)-6-nitrobenzoylchloride (7.60 grams; 0.02 mol) in toluene (10 ml) was added to the mixture in the flask. The mixture, after being stirred overnight at room temperature, was washed with water, dried over sodium sulfate and evaporated to give a dark oil. The oil was chromatographed using silica gel into two fractions, the first using toluene as eluant and the second fraction using an equal mixture of toluene and ethyl acetate gave the desired product as a brown oil which solidified upon standing. Trituration with isopropyl ether resulted in white crystals, melting point 88° C. This product analyzed as follows:

Workup

  1. customglass reaction flask
  2. customequipped with stirrer
  3. additionthermometer, addition funnel
  4. customdrying tube
  5. washwas washed with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customto give a dark oil
  9. customThe oil was chromatographed
  10. additionan equal mixture of toluene and ethyl acetate

Sources & evidence

ORD record
ord-f8e9e5573ba34c5085c7907967cd55bd
Source dataset
uspto-grants-1983_08
Patent number
US04398938

Linked notes

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