Ethylenediamine → HCID 20372262, compound

HRID 1834858Notes

Reaction equation

HRID 1834858 reaction equation
[F:1][C:2]([C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[C:15]#[N:16])([F:12])[C:3]([F:11])([F:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:21](N)[CH2:22][NH2:23]>C(=S)=S.O>[F:1][C:2]([C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[C:15]1[NH:23][CH2:22][CH2:21][N:16]=1)([F:12])[C:3]([F:11])([F:10])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 3301EthylenediamineHCID 20372238HCID 20372238, compound

Product 1

HCID 20372262HCID 20372262, compound

Reagents, catalysts & solvents 2

HCID 6348Carbon DisulfideCatalystHCID 962WaterSolvent

Procedure

2-(α,α,β,β-Tetrafluorophenethyl)benzonitrile, 2.06 g. (0.0074 mole), together with 1.2 g. (0.02 mole) of ethylenediamine and 3 drops of carbon disulfide, is heated in a sealed tube at 160°-165° C. for 18 hours. After cooling in an ice-bath, the tube is opened and the contents are poured into water. The orange gum that separates is washed with water by decantation and then dissolved in ethyl acetate. The ethyl acetate solution is extracted with 3N hydrochloric acid. The combined, ice-cold, acid extracts are rendered strongly alkaline with 40% aqueous sodium hydroxide and the oily base is extracted into ethyl acetate. The washed and dried ethyl acetate extract is concentrated under reduced pressure to a volume of about 25 ml. and 0.6 ml. of 8N ethanolic hydrogen chloride is added. Dilution with an equal volume of absolute ether precipitates the white crystalline hydrochloride salt of the product, m.p. 263°-266° C., sintering at 258° C. Recrystallization from acetone gives a purified sample, m.p. 266°-267° C.

Workup

  1. temperatureAfter cooling in an ice-bath
  2. washThe orange gum that separates is washed with water by decantation
  3. dissolutiondissolved in ethyl acetate
  4. extractionThe ethyl acetate solution is extracted with 3N hydrochloric acid
  5. extractionthe oily base is extracted into ethyl acetate
  6. washThe washed
  7. extractiondried ethyl acetate extract
  8. concentrationis concentrated under reduced pressure to a volume of about 25 ml
  9. additionof 8N ethanolic hydrogen chloride is added
  10. customDilution with an equal volume of absolute ether precipitates the white crystalline hydrochloride salt of the product, m.p. 263°-266° C.
  11. customsintering at 258° C
  12. customRecrystallization from acetone
  13. customgives a purified sample, m.p. 266°-267° C.

Sources & evidence

ORD record
ord-c47e7e244e0a46aabdfdb5f83a6dc783
Source dataset
uspto-grants-1978_01
Patent number
US04071570

Reaction notes

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