Hydrochloric Acid → 2,4,6-Triethyl 1,3,5-triazine-2,4,6-tricarboxylate

HRID 495884Notes

Reaction equation

HRID 495884 reaction equation
Cl.[CH2:2]([O:4][C:5]([C:7]#[N:8])=[O:6])[CH3:3]>>[CH2:2]([O:4][C:5]([C:7]1[N:8]=[C:7]([C:5]([O:4][CH2:2][CH3:3])=[O:6])[N:8]=[C:7]([C:5]([O:4][CH2:2][CH3:3])=[O:6])[N:8]=1)=[O:6])[CH3:3]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 69336Ethyl cyanoformate

Product 1

HCID 134782,4,6-Triethyl 1,3,5-triazine-2,4,6-tricarboxylate

Procedure

Hydrogen chloride gas was bubbled through neat ethylcyanoformate (0.997 ml, 10.1 mmol) until the solution became a white solid, approximately 2 hours. The solid was partitioned between CH2Cl2 and water. The CH2Cl2 layer was collected dried (MgSO4) and concentrated to a white solid. The product was crystallized from hot absolute ethanol to give the title compound (m. p. 169-170° C.). 1H NMR (CDCl3)δ 1.42 (t, 9H, 3x CH3), 4.50 (q, 6H, 3x CH2). 13C NMR (DMSO) δ 14.06 (CH3), 64.02 (CH2), 161.27 (CO), 166.86 (Triazine Ar).

Workup

  1. customa white solid, approximately 2 hours
  2. customThe solid was partitioned between CH2Cl2 and water
  3. customThe CH2Cl2 layer was collected
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated to a white solid
  6. customThe product was crystallized from hot absolute ethanol

Sources & evidence

ORD record
ord-0c1ea90b72b1464d8eb0fa0e67d4a019
Source dataset
uspto-grants-2005_09
Patent number
US06942966B1

Reaction notes

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