Hydrofluoric Acid → 1-(2,2-Dimethyl-3,3-difluoro-indan-1-yl)-5-imidazolecarboxylic acid methyl ester

HRID 5776

반응식

HRID 5776 반응식
[CH3:1][O:2][C:3]([C:5]1[N:9]([CH:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=O)[C:11]2([CH3:21])[CH3:20])[CH:8]=[N:7][CH:6]=1)=[O:4].S(F)(F)(F)[F:23].[FH:27]>>[CH3:1][O:2][C:3]([C:5]1[N:9]([CH:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([F:23])([F:27])[C:11]2([CH3:21])[CH3:20])[CH:8]=[N:7][CH:6]=1)=[O:4]

참가 물질

4

반응물 3

HCID 14917Hydrofluoric AcidHCID 24555Sulfur tetrafluorideHCID 539208951-(2,2-Dimethyl-3-oxoindan-1-yl)-5-imidazolecarboxylic acid methyl ester

생성물 1

HCID 544461901-(2,2-Dimethyl-3,3-difluoro-indan-1-yl)-5-imidazolecarboxylic acid methyl ester수율 68.4%

실험 절차

A mixture of 11.4 g of 1-(2,2-dimethyl-3-oxo-indan-1-yl)-5-imidazolecarboxylic acid methyl ester, 43 g of sulfur tetrafluoride and 160 g of hydrogen fluoride is heated for 24 hours to +50° C. in an acid-resistant autoclave. The pressure is about 7 bars. The unreacted hydrogen fluoride is removed and the residue is taken up with methylene chloride. The organic phase is neutralized with sodium bicarbonate, washed with water, dried with sodium sulfate and concentrated to dryness. Chromatography of the residue at a silica gel column with a diethyl ether/hexane mixture (3:1 by volume) affords 8.4 g of 1-(2,2-dimethyl-3,3-difluoro-indan-1-yl)-5-imidazolecarboxylic acid methyl ester, mp. 96°-97° C.

후처리

  1. temperatureis heated for 24 hours to +50° C. in an acid-resistant autoclave
  2. customThe unreacted hydrogen fluoride is removed
  3. washwashed with water
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-48e222cb04ad453db4f252afa1c90d91
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05246915

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