Hydrochloric Acid → HCID 23371667, compound

HRID 1729197Notes

Reaction equation

HRID 1729197 reaction equation
[N:1]1[C:8]([Cl:9])=[N:7][C:5](Cl)=[N:4][C:2]=1[Cl:3].[NH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11]1.Cl.[Na].[OH-].[Na+].P(=O)(O)(O)O>CC(C)=O>[Cl:9][C:8]1[N:1]=[C:2]([Cl:3])[N:4]=[C:5]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11]2)[N:7]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 1004Phosphoric AcidHCID 7954Cyanuric chlorideHCID 10328IndolineHCID 14798Sodium HydroxideHCID 5360545Sodium

Product 1

HCID 23371667HCID 23371667, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of cyanuric chloride (50 g, 271 mM), acetone (200 ml) and ice (300 g) was added, over ten minutes, a mixture of indoline (32 ml, 286 mM) and 2.5N hydrochloric acid (120 ml). To this stirred mixture was added, over one hour, a solution of sodium secondary phosphate which had been prepared by neutralising 2.5N sodium hydroxide (250 ml) with orthophosphoric acid to PH 7 to 7.5. The mixture was then stirred for one hour, filtered and the resultant solid was washed with water and dried at 80° C. There was thus obtained 2,4-dichloro-6-indolin-1-yl-1,3,5-triazine (72.4 g, 87% yield), a portion of which was recrystallised from toluene, mp 254°-256° C. NMR: DMSOd6 : 3.15-3.3 (2H, t, CH2CH2 --N), 4.05-4.3 (2H, complex, CH2CH2N--) (rotamers), 7.0-7.4 (3H, complex, aromatic), 8.15-8.4 (1H, complex, aromatic).

Workup

  1. additionwas added, over ten minutes
  2. additionTo this stirred mixture was added, over one hour
  3. filtrationfiltered
  4. washthe resultant solid was washed with water
  5. customdried at 80° C

Sources & evidence

ORD record
ord-4320259c9f7f4ac88f8eea83a15ab353
Source dataset
uspto-grants-1994_07
Patent number
US05332737

Reaction notes

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