Ammonia → 1,1-Dimethyl-2-(2-morpholinophenyl)guanidine

HRID 1492274Notes

Reaction equation

HRID 1492274 reaction equation
[CH3:1][N:2]([CH3:18])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)=S.O.O.O.C([O-])(=O)C.[Pb+2].C([O-])(=O)C.[NH3:31].[OH-].[K+]>C(O)C>[CH3:1][N:2]([CH3:18])[C:3]([NH2:31])=[N:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 14797Potassium HydroxideHCID 22456Lead diacetate trihydrateHCID 9711921,1-Dimethyl-3-(2-morpholinophenyl)thiourea

Product 1

HCID 98854071,1-Dimethyl-2-(2-morpholinophenyl)guanidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1,1-dimethyl-3-(2-morpholinophenyl) thiourea (2.65 g prepared as described in Example 232), lead acetate trihydrate (3.8 g), saturated ethanolic ammonia solution (25 ml), potassium hydroxide (1.12 g) and ethanol (20 ml) where heated at 90°-95° C. is a sealed stainless steel pressure vessel for 5 hours. The reaction mixture was filtered and the solid collected washed with ethanol. The washings were added to the filtrate and the volume reduced by evaporation. Ice was added and the resulting solid was collected by filtration, washed with water and dried to give 1,1-dimethyl-2-(2-morpholinophenyl)guanidine (m.p. 141°-142° C.) which was recrystallised from hexane.

Workup

  1. temperatureheated at 90°-95° C.
  2. customfor 5 hours
  3. filtrationThe reaction mixture was filtered
  4. customthe solid collected
  5. washwashed with ethanol
  6. additionThe washings were added to the filtrate
  7. customthe volume reduced by evaporation
  8. additionIce was added
  9. filtrationthe resulting solid was collected by filtration
  10. washwashed with water
  11. customdried

Sources & evidence

ORD record
ord-293a3c261a924de4a86b5297fa2ae379
Source dataset
uspto-grants-1994_12
Patent number
US05373008

Reaction notes

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