Cyclopropylamine → HCID 178471895, compound

HRID 2226492Notes

Reaction equation

HRID 2226492 reaction equation
[F:1][CH:2]([F:28])[O:3][C:4]1[C:5]([F:27])=[C:6]([C:19]([N+:24]([O-:26])=[O:25])=[C:20]([F:23])[C:21]=1[F:22])[C:7]([C:9](=[CH:15]OCC)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:8].[CH:29]1([NH2:32])[CH2:31][CH2:30]1>C(Cl)Cl>[CH:29]1([NH:32][CH:15]=[C:9]([C:7](=[O:8])[C:6]2[C:19]([N+:24]([O-:26])=[O:25])=[C:20]([F:23])[C:21]([F:22])=[C:4]([O:3][CH:2]([F:28])[F:1])[C:5]=2[F:27])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:31][CH2:30]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 54209226Ethyl 2-(3-difluoromethoxy-2,4,5-trifluoro-6-nitrobenzoyl)-3-ethoxyacrylate

Product 1

HCID 178471895HCID 178471895, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The whole of the ethyl 2-(3-difluoromethoxy-2,4,5-trifluoro-6-nitrobenzoyl)-3-ethoxyacrylate [(XVI), R1 =--OCHF2, R3' =NO2, R17 =C2H5, X=X'=F]obtained as described in step (c) above was dissolved in 500 ml of methylene chloride, and 3.5 g (0.06 moles) of cyclopropylamine were added dropwise to the resulting solution, whilst stirring and ice-cooling. The mixture was then stirred for 1 hour, whilst ice-cooling, and then for an additional 1 hour at room temperature, after which the solvent was removed by evaporation under reduced pressure. The resulting residue was subjected to silica gel column chromatography using a 9:1 by volume mixture of toluene and ethyl acetate as the eluent, to give 19.8 g of ethyl 3-cyclopropylamino-2-(3-difluoromethoxy-2,4,5-trifluoro-6-nitrobenzoyl)acrylate as an yellow powder, melting at 105°-106° C.

Workup

  1. temperatureice-cooling
  2. stirringThe mixture was then stirred for 1 hour, whilst ice-
  3. temperaturecooling
  4. customafter which the solvent was removed by evaporation under reduced pressure
  5. additionby volume mixture of toluene and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-2b617f5ab25440bfaf39a5c8a693b8f6
Source dataset
uspto-grants-1994_09
Patent number
US05348961

Reaction notes

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