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

HRID 750967노트

반응식

HRID 750967 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6344Dichloromethane용매2회

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온도
50 °C

실험 절차

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 the title compound.

후처리

  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)

출처 및 근거

ORD 기록
ord-23fd9aba4cfe413892262e8ff7a3b9b2
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07405231B2

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