Dimethylamine → 5-Chloro-2-morpholinophenylguanidine

HRID 1588688Notes

Reaction equation

HRID 1588688 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[C:6]([NH:8][C:9]#[N:10])[CH:7]=1.C[NH:18]C>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[C:6]([NH:8][C:9]([NH2:18])=[NH:10])[CH:7]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 18952323HCID 18952323, compound

Product 1

HCID 1785125605-Chloro-2-morpholinophenylguanidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a similar manner to that described in Example 272, N-(5-chloro-2-morpholinophenyl)cyanamide (2.3 g) in ethanol (10 ml) and a 33% ethanolic solution of dimethylamine (6 ml) were heated under reflux for 4 hours to give 1,1-dimethyl-2-(5-chloro-2-morpholinophenylguanidine (m.p. 135°-138° C.) which was recrystallised from hexane and then was converted into its monofumarate salt (m.p. 223°-225° C.) which was recrystallised from methanol.

Workup

  1. temperatureunder reflux for 4 hours

Sources & evidence

ORD record
ord-f4ac72f7bee24272a68ed04e653cac00
Source dataset
uspto-grants-1993_06
Patent number
US05223498

Reaction notes

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