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

HRID 33494

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. The organic phase was discarded and the aqueous phase acidified with 2M HCl to pH=4, concentrated to a 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 4-(2-[1,2,3]Triazol-1-yl-ethanesulfinylmethyl)-phenol.

Workup

extractionThe mixture was extracted with 3×50 ml sat. NaHCO3-solution and 20 ml water
concentrationconcentrated to a 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-d9c2db7229934015a6ccd109b303a010
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429605B2

Linked notes

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