Ethanol → 2,4,6-Trihydroxymethyl-s-triazine

HRID 411865Notes

Reaction equation

HRID 411865 reaction equation
C([O:3][C:4]([C:6]1[N:11]=[C:10]([C:12](OCC)=[O:13])[N:9]=[C:8]([C:17](OCC)=[O:18])[N:7]=1)=O)C.C(O)C.[BH4-].[Na+].[Cl-].[Ca+2].[Cl-]>ClCCl>[OH:18][CH2:17][C:8]1[N:7]=[C:6]([CH2:4][OH:3])[N:11]=[C:10]([CH2:12][OH:13])[N:9]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 134782,4,6-Triethyl 1,3,5-triazine-2,4,6-tricarboxylateHCID 4311764Sodium borohydrideHCID 5284359Calcium Chloride

Product 1

HCID 223236642,4,6-Trihydroxymethyl-s-triazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,4,6-Triethoxycarbonyl-s-triazine (1 g, 3.36 mmol) is dissolved in dichloromethane (15 mL) and absolute ethanol (25 mL) then cooled to 0° C. before sodium borohydride (127 mg, 3.36 mmol) is added. After 15 minutes calcium chloride (373 mg, 2.97 mmol) is added and the reaction mixture is warmed to room temperature. The reaction mixture is dried to a yellow solid and subjected to soxhlet extraction with ethanol. The ethanol is evaporated to a white solid. The product is crystallized from Methanol and water or purified by silica gel flash column chromatography to give the title compound.

Workup

  1. additionis added
  2. customThe reaction mixture is dried to a yellow solid
  3. extractionextraction with ethanol
  4. customThe ethanol is evaporated to a white solid
  5. customThe product is crystallized from Methanol and water
  6. custompurified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-549c6864854c4a0abf81365ebf54a2fe
Source dataset
uspto-grants-2003_05
Patent number
US06559303B1

Reaction notes

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