Dimethylbarbituric acid → 4-(2-[1,2,3]Triazol-1-yl-ethanesulfinylmethyl)-phenol

HRID 892251Notes

Reaction equation

HRID 892251 reaction equation
CN1C(=O)CC(=O)N(C)C1=O.C([O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][S:23]([CH2:25][CH2:26][N:27]2[CH:31]=[CH:30][N:29]=[N:28]2)=[O:24])=[CH:18][CH:17]=1)C=C>ClCCl.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N:27]1([CH2:26][CH2:25][S:23]([CH2:22][C:19]2[CH:18]=[CH:17][C:16]([OH:15])=[CH:21][CH:20]=2)=[O:24])[CH:31]=[CH:30][N:29]=[N:28]1

Participants

5

Reactant 2

HCID 69860Dimethylbarbituric acidHCID 222420851-[2-(4-Allyloxy-phenylmethanesulfinyl)-ethyl]-1H-[1,2,3]triazole

Product 1

HCID 222420754-(2-[1,2,3]Triazol-1-yl-ethanesulfinylmethyl)-phenolYield 83%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 28.46 g (0.182 mol) 1,3-dimethyl-pyrimidine-2,4,6-trione and 1.81 g (1.57 mmol) tetrakis-(triphenylphosphine)-palladium in 600 ml dichloromethane was added dropwise a solution of 17.70 g (60.75 mmol) 1-[2-(4-allyloxy-phenylmethanesulfinyl)-ethyl]-1H-[1,2,3]triazole and stirring was continued for 6 hours at 45° C. It was allowed to cool down over night. The reaction mixture was extracted with three portions of sodium bicarbonate solution, then the aqueous phase was adjusted to pH 1 and extracted three times with ethyl acetate. The organic extract was dried and evaporated to yield 12.6 g (83%) 4-(2[1,2,3] triazol-1-yl-ethanesulfinylmethyl)-phenol as white solid.

Workup

  1. temperatureto cool down over night
  2. extractionThe reaction mixture was extracted with three portions of sodium bicarbonate solution
  3. extractionextracted three times with ethyl acetate
  4. extractionThe organic extract
  5. customwas dried
  6. customevaporated

Sources & evidence

ORD record
ord-b772262f50cf4758a8c36b32131eb340
Source dataset
uspto-grants-2006_02
Patent number
US07005526B2

Reaction notes

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