Cyclopropylamine → HCID 178418304, compound

HRID 1081407Notes

Reaction equation

HRID 1081407 reaction equation
[F:1][C:2]1[CH:19]=[C:18]([F:20])[C:17]([F:21])=[C:16]([CH3:22])[C:3]=1[C:4]([C:6](=[CH:12]OCC)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].[CH:23]1([NH2:26])[CH2:25][CH2:24]1>C(O)C.CCCCCC>[F:1][C:2]1[CH:19]=[C:18]([F:20])[C:17]([F:21])=[C:16]([CH3:22])[C:3]=1[C:4]([C:6](=[CH:12][NH:26][CH:23]1[CH2:25][CH2:24]1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5]

Participants

5

Reactant 2

HCID 69828CyclopropylamineHCID 54242925Ethyl 2-(2,4,5-trifluoro-6-methylbenzoyl)-3-ethoxyacrylate

Product 1

HCID 178418304HCID 178418304, compoundYield 84.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8058HexaneSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 8.3 g (26 mmol) of ethyl 2-(2,4,5-trifluoro-6-methylbenzoyl)-3-ethoxyacrylate in 30 mL of absolute ethanol at 5° C. was added 1.64 g (29 mmol) of cyclopropylamine. The reaction mixture was stirred at 5° C. for 90 minutes and at room temperature for 2 hours. The solution was concentrated to give a brown oil which was dissolved in hexane and reconcentrated to give a tan solid. Recrystallization from hexane gave 7.2 g of colorless crystals, mp 69°-72° C.

Workup

  1. concentrationThe solution was concentrated
  2. customto give a brown oil which
  3. customto give a tan solid
  4. customRecrystallization from hexane

Sources & evidence

ORD record
ord-561754730f5748ea9748363a9de0e702
Source dataset
uspto-grants-1996_12
Patent number
US05585491

Reaction notes

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