Cycloheptylamine → 6-chloro-N-(3-chloro-4-methoxyphenyl)-N'-cycloheptyl-[1,3,5]triazine-2,4-diamine

HRID 1375476Notes

Reaction equation

HRID 1375476 reaction equation
[N:1]1[C:8](Cl)=[N:7][C:5](Cl)=[N:4][C:2]=1[Cl:3].[Cl:10][C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[NH2:14].C(=O)([O-])[O-].[K+].[K+].[CH:26]1([NH2:33])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>CC(C)=O>[Cl:3][C:2]1[N:1]=[C:8]([NH:14][C:13]2[CH:15]=[CH:16][C:17]([O:18][CH3:19])=[C:11]([Cl:10])[CH:12]=2)[N:7]=[C:5]([NH:33][CH:26]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[N:4]=1

Participants

6

Reactant 4

HCID 2899CycloheptylamineHCID 7954Cyanuric chlorideHCID 11430Potassium CarbonateHCID 214413-Chloro-4-methoxyaniline

Product 1

HCID 218970216-chloro-N-(3-chloro-4-methoxyphenyl)-N'-cycloheptyl-[1,3,5]triazine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A convenient, one-pot synthesis of 6-chloro-N-(3-chloro-4-methoxyphenyl)-N′-cyclopheptyl-[1,3,5]triazine-2,4-diamine was carried out as follows. To cyanuric chloride (50 g) dissolved in acetone was added a solution of 3-chloro-4-methoxyaniline (42.5 g) in acetone at 0–5° C. followed by the addition of potassium carbonate (112 g). The reaction mass was maintained at the same temperature for about 1 hour. The progress of the reaction was monitored by TLC. When the reaction was complete, cycloheptylamine (29 g dissolved in acetone) was added at 0–10° C. The reaction mass was maintained under reflux for about 2–3 hours. Completion of the reaction was checked by TLC. The reaction mass was cooled to 20–30° C. and poured over crushed ice under stirring. The solid compound thrown out was filtered and dried. The crude compound was then recrystallised from ethylacetate (Wt. 50 g Y: 48%).

Workup

  1. temperatureThe reaction mass was maintained at the same temperature for about 1 hour
  2. temperatureThe reaction mass was maintained
  3. temperatureunder reflux for about 2–3 hours
  4. temperatureThe reaction mass was cooled to 20–30° C.
  5. additionpoured
  6. customover crushed ice
  7. filtrationThe solid compound thrown out was filtered
  8. customdried
  9. customThe crude compound was then recrystallised from ethylacetate (Wt. 50 g Y: 48%)

Sources & evidence

ORD record
ord-03ef1b006dcc48b69db47595a83ad36f
Source dataset
uspto-grants-2007_01
Patent number
US07169784B2

Reaction notes

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