Acrylonitrile → HCID 459422, compound

HRID 1030922Notes

Reaction equation

HRID 1030922 reaction equation
Cl.[F:2][C:3]([F:12])([F:11])[C:4]1[CH:5]=[C:6]([NH2:10])[CH:7]=[CH:8][CH:9]=1.[C:13](#[N:16])[CH:14]=[CH2:15].C(NCC)C.[OH-].[Na+]>>[F:2][C:3]([F:11])([F:12])[C:4]1[CH:5]=[C:6]([NH:10][CH2:15][CH2:14][C:13]#[N:16])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 4

HCID 7855AcrylonitrileHCID 8021DiethylamineHCID 14798Sodium HydroxideHCID 200755Alpha,alpha,alpha-trifluoro-M-toluidine hydrochloride

Product 1

HCID 459422HCID 459422, compoundYield 45%

Conditions

Temperature
180 °C

Procedure

A mixture of 70 parts of 3-(trifluoromethyl)benzenamine hydrochloride, 26.5 parts of 2-propenenitrile and 36.5 parts of N-ethylethanamine was stirred for 2.5 hours at 180° C. After cooling to 0° C., the whole was treated with a sodium hydroxide solution. The product was extracted with dichloromethane. The extract was washed with water, dried, filtered and evaporated, yielding 34.5 parts (45%) of 3-[[3-(trifluoromethyl)phenyl]amino]propanenitrile as a residue (int. 105).

Workup

  1. temperatureAfter cooling to 0° C.
  2. extractionThe product was extracted with dichloromethane
  3. washThe extract was washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-708317595f0b4c188a3c3d06effdcb42
Source dataset
uspto-grants-1992_04
Patent number
US05106973

Reaction notes

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