Cyanuric chloride → 4,6-dichloro-2-ethoxycarbonylmethylamino-S-triazine

HRID 325969

Reaction equation

HRID 325969 reaction equation
[N:1]1[C:8]([Cl:9])=[N:7][C:5](Cl)=[N:4][C:2]=1[Cl:3].C(=O)(O)[O-].[Na+].Cl.[CH2:16]([O:18][C:19](=[O:22])[CH2:20][NH2:21])[CH3:17]>CC(C)=O>[Cl:9][C:8]1[N:1]=[C:2]([Cl:3])[N:4]=[C:5]([NH:21][CH2:20][C:19]([O:18][CH2:16][CH3:17])=[O:22])[N:7]=1

Participants

5

Reactant 3

HCID 7954Cyanuric chlorideHCID 516892Sodium BicarbonateHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 147462614,6-dichloro-2-ethoxycarbonylmethylamino-S-triazineYield 51.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 10 g of ice water was added 1.84 g of cyanuric chloride dissolved in 50 ml of acetone. To this solution kept at an internal temperature of 0° to 5° C. under stirring were added 1.68 g of sodium bicarbonate and 1.40 g of glycine ethylester hydrochloride and the mixture was stirred at said temperature for 30 minutes. The reaction product was extracted with ethyl acetate and dried with sodium sulfate. Then, ethyl acetate was distilled out and separated crystal was recrystallized from cyclohexane to obtain 1.3 g of 4,6-dichloro-2-ethoxycarbonylmethylamino-S-triazine which had a melting point of 89° to 90.5° C.

Workup

  1. customkept at an internal temperature of 0° to 5° C.
  2. stirringthe mixture was stirred
  3. customfor 30 minutes
  4. extractionThe reaction product was extracted with ethyl acetate
  5. dry with materialdried with sodium sulfate
  6. distillationThen, ethyl acetate was distilled out
  7. customseparated crystal
  8. customwas recrystallized from cyclohexane

Sources & evidence

ORD record
ord-6eb8874b925d4cb5a681e519d504615f
Source dataset
uspto-grants-1984_04
Patent number
US04443531

Linked notes

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