Propylamine → HCID 178457521, compound

HRID 1588679Notes

Reaction equation

HRID 1588679 reaction equation
C[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.[CH2:19]([NH2:22])[CH2:20][CH3:21].O.O.O.[C:26]([O-])(=O)[CH3:27].[Pb+2].[C:31]([O-])(=O)[CH3:32].[OH-].[K+].[C:37]([OH:44])(=[O:43])/[CH:38]=[CH:39]/[C:40]([OH:42])=[O:41]>CO.C(O)C>[C:37]([OH:44])(=[O:43])/[CH:38]=[CH:39]/[C:40]([OH:42])=[O:41].[CH2:19]([NH:22][C:3]([NH:2][CH2:18][CH2:26][CH3:27])=[N:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1)[CH2:20][CH3:21].[CH2:19]([NH:22][C:3]([NH:2][CH2:18][CH2:31][CH3:32])=[N:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1)[CH2:20][CH3:21]

Participants

8

Reactant 5

HCID 7852Propylamine2×HCID 14797Potassium HydroxideHCID 22456Lead diacetate trihydrateHCID 444972Fumaric AcidHCID 9711921,1-Dimethyl-3-(2-morpholinophenyl)thiourea

Product 1

HCID 178457521HCID 178457521, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A mixture of 1,1-dimethyl-3-(2-morpholinophenyl)thiourea (2.65 g prepared as described in Example 232), n-propylamine (1.6 ml), lead acetate trihydrate (3.8 g), potassium hydroxide (1.2 g) and ethanol (25 ml) was heated under reflux for 4 hours. A further amount of n-propylamine (1.6 ml) was added and the mixture heated under reflux for a further 8 hours. The reaction mixture yielded a residue which was extracted with ether. The extract was decolourised with charcoal, filtered and the solvent removed to leave a sticky solid which was dissolved in methanol (10 ml) and treated with fumaric acid to give 1,3-di-(n-propyl)-2-(2-morpholinophenyl)guanidine hemifumarate (m.p. 212°-214° C.) which was recrystallised from a 1:2 mixture of methanol and ether.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. temperaturethe mixture heated
  4. temperatureunder reflux for a further 8 hours
  5. customThe reaction mixture yielded a residue which
  6. extractionwas extracted with ether
  7. filtrationfiltered
  8. customthe solvent removed
  9. customto leave a sticky solid which

Sources & evidence

ORD record
ord-bec48f64d5ee40439715bb5535495988
Source dataset
uspto-grants-1993_06
Patent number
US05223498

Reaction notes

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