Ammonia → 1-(2-(4-Isothiocyanatophenoxy)ethyl)pyrrolidine

HRID 1076833Notes

Reaction equation

HRID 1076833 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:16](=S)=[S:17].N>C(O)C>[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([N:13]=[C:16]=[S:17])=[CH:14][CH:15]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6348Carbon DisulfideHCID 64937494-(2-(Pyrrolidin-1-yl)ethoxy)aniline

Product 1

HCID 118461221-(2-(4-Isothiocyanatophenoxy)ethyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

4-(2-Pyrrolidin-1-ylethoxy)aniline (17.3 g.) in ethanol (20 ml.) is added dropwise to a mixture of ethanol (55 ml.), carbon disulphide (10 ml.) and aqueous ammonia (density = 0.88, 20 ml.) at 0°C. After 2 hours the solid is collected and washed with acetone, m.p. 143° - 150°C. (dec.). This solid (23.6 g.), chloroform (114 ml.) and triethylamine (11.9 ml.) are stirred, and ethyl chloroformate (8.6 ml.) added with cooling so that the temperature remains below 0°C. After stirring for 30 minutes below 0°C. and 1 hour at 20°C., excess of 10% sodium hydroxide is added. The chloroform is separated, washed with water, dried and evaporated. The residue is dissolved in benzene and the solution filtered through alumina. The filtrate is evaporated and the residue distilled to give 4-(2-pyrrolidin-1-ylethoxy)phenyl isothiocyanate, b.p. 160° - 168°C./0.2 mm.

Workup

  1. customAfter 2 hours the solid is collected
  2. washwashed with acetone, m.p. 143° - 150°C. (dec.)
  3. additionethyl chloroformate (8.6 ml.) added
  4. temperaturewith cooling so that the temperature
  5. customremains below 0°C
  6. stirringAfter stirring for 30 minutes below 0°C. and 1 hour at 20°C., excess of 10% sodium hydroxide
  7. additionis added
  8. customThe chloroform is separated
  9. washwashed with water
  10. customdried
  11. customevaporated
  12. dissolutionThe residue is dissolved in benzene
  13. filtrationthe solution filtered through alumina
  14. customThe filtrate is evaporated
  15. distillationthe residue distilled

Sources & evidence

ORD record
ord-e71717069173479e983c7ee1f0aaef0f
Source dataset
uspto-grants-1976_05
Patent number
US03957999

Reaction notes

Loading…