Dimethylamine → Urea, N,N-dimethyl-N'-(4-(4-morpholinyl)-6-propyl-1,3,5-triazin-2-yl)-

HRID 1031870Notes

Reaction equation

HRID 1031870 reaction equation
[CH3:1][NH:2][CH3:3].[O:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:15]=[C:14]([CH2:16][CH2:17][CH3:18])[N:13]=[C:12]([NH:19][C:20](=[O:28])OC3C=CC=CC=3)[N:11]=2)[CH2:6][CH2:5]1>ClCCl>[CH3:1][N:2]([CH3:3])[C:20]([NH:19][C:12]1[N:11]=[C:10]([N:7]2[CH2:6][CH2:5][O:4][CH2:9][CH2:8]2)[N:15]=[C:14]([CH2:16][CH2:17][CH3:18])[N:13]=1)=[O:28]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 3080144Carbamic acid, (4-(4-morpholinyl)-6-propyl-1,3,5-triazin-2-yl)-, phenyl ester2×

Product 1

HCID 3080162Urea, N,N-dimethyl-N'-(4-(4-morpholinyl)-6-propyl-1,3,5-triazin-2-yl)-Yield 39.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A gaseous stream of dimethylamine is passed through a solution of 5 g (0.0145 mol) of phenyl (4-morpholino-6-propyl-1,3,5-triazin-2-yl)carbamate (compound 28) in 100 ml of anhydrous dichloromethane for three hours at a temperature of 20° C. The mixture is then allowed to stand for 12 hours. It is washed successively with a dilute sodium hydroxide solution and with water. The organic phase is dried over sodium sulfate and the solvent is evaporated under reduced pressure. The residue obtained crystallizes in a 50:50 mixture (v/v) of ethyl acetatehexane. 1.7 g of N,N-dimethyl-N'-(4-morpholino-6-propyl-1,3,5-triazin-2-yl)-urea is obtained.

Workup

  1. washIt is washed successively with a dilute sodium hydroxide solution and with water
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. customthe solvent is evaporated under reduced pressure
  4. customThe residue obtained
  5. customcrystallizes in a 50:50 mixture (v/v) of ethyl acetatehexane

Sources & evidence

ORD record
ord-f822b048092e43788f670238751587ca
Source dataset
uspto-grants-1990_09
Patent number
US04956363

Reaction notes

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