Sodium Hydroxide → 1-{[2-(2,4-Difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole monomethanesulfonate

HRID 543202

반응식

HRID 543202 반응식
Cl.[F:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[C:10](=[O:17])[CH2:11][N:12]1[CH:16]=[N:15][CH:14]=[N:13]1.[I-].[CH3:19][S+:20]([CH3:23])(C)=[O:21].[OH-:24].[Na+]>C1(C)C=CC=CC=1.CCCCCCCCCCCCCC[N+](C)(C)C>[CH3:23][S:20]([OH:17])(=[O:21])=[O:24].[F:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[C:10]1([O:17][CH2:19]1)[CH2:11][N:12]1[CH:16]=[N:15][CH:14]=[N:13]1

참가 물질

6

반응물 3

HCID 14798Sodium HydroxideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 130596991-(2,4-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-ethanone hydrochloride (1:1)

생성물 1

HCID 130597001-{[2-(2,4-Difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole monomethanesulfonate수율 56%

시약·촉매·용매 2

HCID 14251Tetradecyltrimethylammonium촉매HCID 1140Toluene용매

반응 조건

온도
0 °C

실험 절차

2',4'-Difluoro-2-(1H-1,2,4-triazol-1-yl)acetophenone hydrochloride (59.6 g, 0.23M), trimethylsulphoxonium iodide (50.6 g, 0.23M) and cetrimide (2.1 g) were stirred in a mixture of toluene (370 ml) and 20% w/w aqueous sodium hydroxide at 60° for 3 hours. The toluene layer was separated and concentrated to 110 ml then diluted with ethyl acetate (150 ml). A solution of methanesulphonic acid (16.6 g, 0.172M) in ethyl acetate (20 ml) was added. More ethyl acetate (100 ml) was added and the mixture was stirred at 0° C. for one hour then filtration of the precipitate gave the title compound (43 g, 56%).

후처리

  1. customThe toluene layer was separated
  2. concentrationconcentrated to 110 ml
  3. additionthen diluted with ethyl acetate (150 ml)
  4. additionA solution of methanesulphonic acid (16.6 g, 0.172M) in ethyl acetate (20 ml) was added
  5. additionMore ethyl acetate (100 ml) was added
  6. filtrationfiltration of the precipitate

출처 및 근거

ORD 기록
ord-0f30691268ca44be918bb9d9fd101fac
출처 데이터셋
uspto-grants-1987_04
특허 번호
US04661507

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