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

HRID 719409Notes

Reaction equation

HRID 719409 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-f7b5367d4135416b914433cae9817839
Source dataset
uspto-grants-2006_11
Patent number
US07132423B2

Reaction notes

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