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

HRID 33494

反応式

HRID 33494 の反応式
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

参加物

5

反応物 2

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

生成物 1

HCID 222420754-(2-[1,2,3]Triazol-1-yl-ethanesulfinylmethyl)-phenol収率 97.5%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
50 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-d9c2db7229934015a6ccd109b303a010
出典データセット
uspto-grants-2008_09
特許番号
US07429605B2

関連ノート

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