Water → 4-(p-Toluenesulfonylmethyl)-2,6-dihydroxymethyl-s-triazine

HRID 411866Notes

Reaction equation

HRID 411866 reaction equation
O[CH2:2][C:3]1[N:8]=[C:7]([CH2:9][OH:10])[N:6]=[C:5]([CH2:11][OH:12])[N:4]=1.N1C=CC=CC=1.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.O>C(Cl)Cl>[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25]([CH2:2][C:3]2[N:8]=[C:7]([CH2:9][OH:10])[N:6]=[C:5]([CH2:11][OH:12])[N:4]=2)(=[O:27])=[O:26])=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 223236642,4,6-Trihydroxymethyl-s-triazine

Product 1

HCID 223236944-(p-Toluenesulfonylmethyl)-2,6-dihydroxymethyl-s-triazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2,4,6-Trihydroxymethyl-s-triazine (1 eq.) is dissolved in an excess of pyridine. p-Toluenesulfonylchloride (0.6 eq.) in CH2Cl2 is added and the reaction mixture is stirred overnight. The solvent volume is reduced to a slurry to which water and dichloromethane are added and the resulting mixture is extracted with CH2Cl2. The combined CH2Cl2 layers are dried (MgSO4) and concentrated to an oil. The oil is purified by silica gel flash column chromatography to give the title compound.

Workup

  1. additionare added
  2. extractionthe resulting mixture is extracted with CH2Cl2
  3. dry with materialThe combined CH2Cl2 layers are dried (MgSO4)
  4. concentrationconcentrated to an oil
  5. customThe oil is purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-148b523b2e064006b5f348fd088437fa
Source dataset
uspto-grants-2003_05
Patent number
US06559303B1

Reaction notes

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