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

HRID 1768068Notes

Reaction equation

C([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][S:12]([CH2:14][CH2:15][N:16]2[CH:20]=[CH:19][N:18]=[N:17]2)=[O:13])=[CH:7][CH:6]=1)C=C.CN1C(=O)CC(=O)N(C)C1=O>ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:16]1([CH2:15][CH2:14][S:12]([CH2:11][C:8]2[CH:7]=[CH:6][C:5]([OH:4])=[CH:10][CH:9]=2)=[O:13])[CH:20]=[CH:19][N:18]=[N:17]1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 1.00 g (3.43 mmol) 1-[2-(4-Allyloxy-phenylmethanesulfinyl)-ethyl]-1H-[1,2,3]triazole in 60 ml dichloromethane was added to a solution of 1.61 g (10.3 mmol) 1,3-dimethylbarbituric acid and 102 mg (0.09 mmol) Pd(PPh3)4 in 30 ml dichloromethane and stirred for 5 h at 50° C. The mixture was extracted with 3×50 ml sat. NaHCO3-solution and 20 ml water. Thee organic phase was discarded and the aqueous phase acidified with 2M HCl to pH=4, concentrated to volume of 50 ml and adjusted to pH=1. After five extractions with ethyl acetate, the organic extracts were combined and dried over MgSO4. After evaporation the residue was purified by chromatography on silica gel (dichloromethane/methanol 100:2) to yield 0.84 g (97%) of the title compound.

Workup

extractionThe mixture was extracted with 3×50 ml sat. NaHCO3-solution and 20 ml water
concentrationconcentrated to volume of 50 ml
extractionAfter five extractions with ethyl acetate
dry with materialdried over MgSO4
customAfter evaporation the residue
customwas purified by chromatography on silica gel (dichloromethane/methanol 100:2)

Sources & evidence

ORD record: ord-f2091616bed7453383e85900dd4a82d6
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07235574B2

Reaction notes

Loading…