3-Morpholinopropyl isothiocyanate → HCID 22118525, compound

HRID 365284Notes

Reaction equation

HRID 365284 reaction equation
[Br:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][N:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[CH2:8][CH2:9][CH2:10][NH2:11])=[CH:4][CH:3]=1.[O:20]1[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][CH2:28][N:29]=[C:30]=[S:31])[CH2:22][CH2:21]1>C(Cl)(Cl)Cl.O1CCN(CCCN=C=S)CC1>[Br:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][N:7]([CH2:8][CH2:9][CH2:10][NH:11][C:30]([NH:29][CH2:28][CH2:27][CH2:26][N:23]2[CH2:24][CH2:25][O:20][CH2:21][CH2:22]2)=[S:31])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 1417453-Morpholinopropyl isothiocyanateHCID 22118499HCID 22118499, compound

Product 1

HCID 22118525HCID 22118525, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 1417453-Morpholinopropyl isothiocyanateCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of N-(4-bromobenzyl)-N-(pyridin-2-yl)pro-pane-1,3-diamine (1.0 g, 3.123 mmol) in chloroform (40 ml) was added 3-morpholinopropyl isothiocyanate (593 mg, 3.123 mmol) and the reaction mixture was stirred for 20 h at reflux temperature. To the reaction mixture was added 10 drops of 3-morpholinopropyl isothiocyanate and the reaction mixture was stirred for an additional 4 h at reflux temperature. The volatiles were evaporated in vacuo and the residue (2.05 g) was dissolved in ethyl acetate (20 ml) and left over night at room temperature. The precipitate was filtered off and washed with ethyl acetate and dried affording 1.20 g (76%) of the title compound as a solid.

Workup

  1. temperatureat reflux temperature
  2. stirringthe reaction mixture was stirred for an additional 4 h
  3. temperatureat reflux temperature
  4. customThe volatiles were evaporated in vacuo
  5. dissolutionthe residue (2.05 g) was dissolved in ethyl acetate (20 ml)
  6. waitleft over night at room temperature
  7. filtrationThe precipitate was filtered off
  8. washwashed with ethyl acetate
  9. customdried

Sources & evidence

ORD record
ord-3bbdcfb309dd4e2aa7cf5c83d0730c30
Source dataset
uspto-grants-2000_10
Patent number
US06127343

Reaction notes

Loading…