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

HRID 2216470Notes

Reaction equation

HRID 2216470 reaction equation
[N:1]1[C:8]([Cl:9])=[N:7][C:5]([Cl:6])=[N:4][C:2]=1Cl.Cl[C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[NH2:19])[O:14][CH3:15].[OH-].[Na+].[ClH:22]>CC(C)=O>[Cl:22][C:12]1[CH:11]=[C:18]([NH:19][C:2]2[N:1]=[C:8]([Cl:9])[N:7]=[C:5]([Cl:6])[N:4]=2)[CH:17]=[CH:16][C:13]=1[O:14][CH3:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7954Cyanuric chlorideHCID 14798Sodium HydroxideHCID 4074322-Chloro-4-methoxyaniline

Product 1

HCID 21896921(3-Chloro-4-methoxy-phenyl)-(4,6-dichloro-[1,3,5]triazin-2-yl)-amineYield 96%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To cyanuric chloride (36.911 g, 200.0 mmol) dissolved in acetone (250 mL) stirring at approximately 0-5° C. (ice-water bath), was added a solution of 3-chloro-p-anisidine (31.528 g, 200.0 mmol) in acetone (150 mL) followed by the addition of NaOH solution (80 mL, 2.5 N, 200.0 mmol). The reaction mixture was allowed to stir at approximately 0-5° C. (ice-water bath) for about 1 hour. The reaction mixture was then poured over crushed ice and neutralized with 10% HCl (aq). The resulting solid was washed with water and dried overnight under vacuum to afford 101 (58.3 g, 96%), mp 165° C.; HPLC: YMC Pack Pro C18, 40:30:30 [KH2PO4 (0.01M, pH 3.2):CH3OH:CH3CN], 264 nm, Rt 24.3 min, 97.8% purity); MS (ESI): m/z 305 (M+H, 100), 283 (26.3), 271 (26.9), 269 (75.2), 139 (16.2).

Workup

  1. additionThe reaction mixture was then poured
  2. customover crushed ice
  3. washThe resulting solid was washed with water
  4. customdried overnight under vacuum

Sources & evidence

ORD record
ord-fd0487fd3bac47e592e9acfc5bd4f40d
Source dataset
uspto-grants-2006_09
Patent number
US07112587B2

Reaction notes

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