Carbodiimide → N-[3-(dimethyl-amino)]propyl-N'-(3-morpholino)propyl-carbodiimide

HRID 341909Notes

Reaction equation

HRID 341909 reaction equation
[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][CH2:5][NH:6][C:7]([NH:9][CH2:10][CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)=S.N=C=N>CC(C)=O.[Hg]=O>[CH3:19][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][N:6]=[C:7]=[N:9][CH2:10][CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1

Participants

5

Reactant 2

HCID 160435CarbodiimideHCID 54184092N-[3-(dimethylamino)]propyl-N'-(3-morpholino)propyl-thiourea3×

Product 1

HCID 10923093N-[3-(dimethyl-amino)]propyl-N'-(3-morpholino)propyl-carbodiimideYield 60%

Reagents, catalysts & solvents 2

HCID 30856Mercuric oxideCatalystHCID 180AcetoneSolvent

Procedure

In 35 ml of acetone was dissolved 2.7 g (10 mmol) of N-[3-(dimethylamino)]propyl-N'-(3-morpholino)propyl -thiourea (Compound (1)). Further, 4.2 g (20 mmol) of mercury oxide was added, and the resulting mixture was stirred for 2 hours under reflux. Then, the reaction mixture was allowed to cool and filtered. The solvent was distilled off to obtain a crude product. This product was evaporated under reduced pressure to obtain 1.5 g (yield: 60%) of N-[3-(dimethyl-amino)]propyl-N'-(3-morpholino)propyl-carbodiimide (Compound (2) in the following reaction formula (1)). Its boiling point (b.p.) was from 125° to 128° C./0.2 mmHg. NMR spectrum data of Compound (2) are shown below.

Workup

  1. temperatureunder reflux
  2. temperatureto cool
  3. filtrationfiltered
  4. distillationThe solvent was distilled off
  5. customto obtain a crude product
  6. customThis product was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b049bfa0a79e480e9607b1981e115b55
Source dataset
uspto-grants-1999_01
Patent number
US05856479

Reaction notes

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