Triethylamine → HCID 20393504, compound

HRID 1862795Notes

Reaction equation

HRID 1862795 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][C:8]=2[C:14]([F:17])([F:16])[F:15])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:27]([C:31]1([C:34](Cl)=[O:35])[CH2:33][CH2:32]1)[CH2:28][CH2:29][CH3:30]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:13]=[CH:12][C:10]([NH:11][C:34]([C:31]3([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:33][CH2:32]3)=[O:35])=[CH:9][C:8]=2[C:14]([F:15])([F:16])[F:17])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 7260924-(4-chlorophenoxy)-3-(trifluoromethyl)anilineHCID 54546667HCID 54546667, compound

Product 1

HCID 20393504HCID 20393504, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution containing 2.9 g (0.01 mole) of the amine prepared in Example 4 (b), and 1.0 g (0.01 mole) of triethylamine in 50 ml of tetrahydrofuran was added dropwise 1.7 g (0.01 mole) of 1-butylcyclopropanecarboxylic acid chloride. The mixture was stirred and heated at 60° C. for 0.5 hour, poured into ice water and extracted with ether. The ether extract was dried and concentrated under reduced pressure. The residual yellow syrup was crystallized from hexane to give 3.3 g (80%) of product as a tan solid, m.p. 104°-106° C.

Workup

  1. extractionextracted with ether
  2. extractionThe ether extract
  3. customwas dried
  4. concentrationconcentrated under reduced pressure
  5. customThe residual yellow syrup was crystallized from hexane

Sources & evidence

ORD record
ord-c74230c605c04a6780b03bce5248efb1
Source dataset
uspto-grants-1979_09
Patent number
US04166735

Reaction notes

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