Cyclopropylamine → 3-Cyclopropylamino-2-(2,3,4,5-tetrafluorobenzoyl)acrylonitrile

HRID 1788977Notes

Reaction equation

HRID 1788977 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.C(O[CH:8]=[C:9]([C:12](=[O:23])[C:13]1[CH:18]=[C:17]([F:19])[C:16]([F:20])=[C:15]([F:21])[C:14]=1[F:22])[C:10]#[N:11])C>C(Cl)(Cl)Cl.C(O)C.CCCCCC>[CH:1]1([NH:4][CH:8]=[C:9]([C:12](=[O:23])[C:13]2[CH:18]=[C:17]([F:19])[C:16]([F:20])=[C:15]([F:21])[C:14]=2[F:22])[C:10]#[N:11])[CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 69828CyclopropylamineHCID 53655523HCID 53655523, compound

Product 1

HCID 867417183-Cyclopropylamino-2-(2,3,4,5-tetrafluorobenzoyl)acrylonitrileYield 86.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6212ChloroformSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of cyclopropylamine (3.3 g) in chloroform (20 ml) is added dropwise to a solution of 3-ethoxy-2-(2,3,4,5-tetrafluorobenzoyl)acrylonitrile (14.0 g) in chloroform (50 ml) with maintaining the internal temperature between 6° C. and 8° C. by using an ice bath. The mixture is allowed to stand overnight at room temperature and then concentrated under vacuum to yield an orange oily residue. The oily residue is dissolved in ethanol and the ethanol is removed in vacuum to afford a crystalline residue. The residue is dissolved in hexane and washed with a 20:1 mixture of hexane and ethanol to yield 3-cyclopropylamino-2-(2,3,4,5-tetrafluorobenzoyl)acrylonitrile (12.6 g) as pale yellow prisms, m.p. 88°-89° C.

Workup

  1. temperaturewith maintaining the internal temperature between 6° C. and 8° C.
  2. concentrationconcentrated under vacuum
  3. customto yield an orange oily residue
  4. customthe ethanol is removed in vacuum
  5. customto afford a crystalline residue
  6. washwashed with a 20:1 mixture of hexane and ethanol

Sources & evidence

ORD record
ord-18a86dc2dfb6483390cdb8493d259c89
Source dataset
uspto-grants-1987_08
Patent number
US04686221

Reaction notes

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