Cyanuric chloride → (3-Chloro-4-methoxy-phenyl)-(4,6-dichloro-[1,3,5]triazin-2-yl)-amine

HRID 915156Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([NH:10]C2N=C(NC3CCCCCC3)N=C(N(C)C3CCN(C)CC3)N=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[N:34]1[C:41]([Cl:42])=[N:40][C:38]([Cl:39])=[N:37][C:35]=1Cl.ClC1C=C(C=CC=1OC)N.[OH-].[Na+]>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:35]2[N:34]=[C:41]([Cl:42])[N:40]=[C:38]([Cl:39])[N:37]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

Reactant 4

HCID 7954Cyanuric chloride

HCID 14798Sodium Hydroxide

HCID 214413-Chloro-4-methoxyaniline

HCID 21896974N-(3-Chloro-4-methoxy-phenyl)-N'-cycloheptyl-N''-methyl-N''-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine

Product 1

HCID 21896921(3-Chloro-4-methoxy-phenyl)-(4,6-dichloro-[1,3,5]triazin-2-yl)-amine

Procedure

This reaction scheme illustrates synthesis of compound 137 by reaction of cyanuric chloride with 3-chloro-4-methoxyaniline using sodium hydroxide (NaOH) as base at 0-5° C. to yield (3-chloro-4-methoxy phenyl)-(4,6-dichloro-[1,3,5]triazine-2-yl)amine (compound 101), which on reaction with cycloheptylamine in presence of NaOH under reflux gave 6-chloro-N-(3-Chloro-4-methoxyphenyl)-N′-cycloheptyl-[1,3,5]triazine-2,4-diamine (compound 133). Compound 133 on reaction with 1-methyl-(4-methylamino)piperidine yields, the final compound 137.

Workup

customThis reaction scheme
customat 0-5° C.

Sources & evidence

ORD record: ord-8da43361c0c647c0b5cd46509fcb4f1c
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265114B2

Reaction notes

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