Triethylamine → HCID 86664075, compound

HRID 1960054Notes

Reaction equation

HRID 1960054 reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C.[F:25][C:26](=[C:32]([F:34])[F:33])[CH2:27][CH2:28][C:29](O)=[O:30]>C(Cl)Cl>[F:25][C:26](=[C:32]([F:34])[F:33])[CH2:27][CH2:28][C:29]([N:3]([O:4][CH3:5])[CH3:2])=[O:30]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27824474,5,5-trifluoropent-4-enoic Acid

Product 1

HCID 86664075HCID 86664075, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,O-dimethylhydroxyamine hydrochloride (3.5 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (6.9 g) and triethylamine (9.2 mL) were added to a solution of 4,5,5-trifluoropent-4-enoic acid (CAS No. 110003-22-0 (5.0 g)) in methylene chloride solution (64 mL) in a cold-water bath and stirring was carried out at room temperature overnight. The reaction solution was concentrated and diluted with ethyl acetate. The dilute solution was washed with 1 N hydrochloric acid, water and saturated brine; dried with anhydrous sodium sulfate; and concentrated to obtain the title compound (6.4 g) having the following physical properties:

Workup

  1. concentrationThe reaction solution was concentrated
  2. additiondiluted with ethyl acetate
  3. washThe dilute solution was washed with 1 N hydrochloric acid, water and saturated brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationand concentrated

Sources & evidence

ORD record
ord-bb9cb62035cf4b92b324c813c2d2a009
Source dataset
uspto-grants-2013_04
Patent number
US08410281B2

Reaction notes

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