Water → HCID 10737609, 화합물

HRID 327170노트

반응식

HRID 327170 반응식
[F:1][C:2]([F:10])([F:9])[C:3]([OH:8])([CH3:7])[C:4](O)=[O:5].S(Cl)(Cl)=O.[C:15]([C:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][C:18]=1[S:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)#[N:16].O>CN(C)C(=O)C>[C:15]([C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:4](=[O:5])[C:3]([OH:8])([CH3:7])[C:2]([F:10])([F:9])[F:1])=[CH:19][C:18]=1[S:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)#[N:16]

참가 물질

6

반응물 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 27751253,3,3-Trifluoro-2-hydroxy-2-methylpropanoic acidHCID 10585340HCID 10585340, 화합물

생성물 1

HCID 10737609HCID 10737609, 화합물수율 94.8%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

To a stirred, cooled (-20° C.) solution of 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid (1.62 g 10.2 mmol) in N,N-dimethylacetamide (15 mL) was rapidly added thionyl chloride (1.30 g, 10.9 mmol) and the mixture (a precipitate formed after a few minutes) stirred at -20° C. to -5° C. for 1 hour. 4-Cyano-3-phenylthiobenzenamine (1.55 g, 6.85 mmol) was then added in one portion and the mixture allowed to stir at room temperature overnight. The solution was poured into water, extracted with ethyl ether (2×100 mL); the etheral extracts dried (MgSO4), filtered and the solvent removed in vacuo. The residue was chromatographed on 315 g of silica gel using a ethyl ether (0%, 10%, and 20%) in methylene chloride gradient. The proper fractions were combined, the solvent removed in vacuo and the residue dissolved in a mixture of 100 mL hexane and 150 mL methylene chloride. Most of the methylene chloride was distilled off as the solution was scratched to induce crystal growth. After cooling the solid was collected and dried at 85° C. /0.1 mm to yield the title propanamide (2.38 g, 91%); mp 111°-113° C. 1H--NMR (250 MHz, CDCl3): 1.67 (s, 3H, CH 3), 3.68 (s, 1H, OH), 7.27 (d, 1H, J=1.9 Hz, aromatic), 7.40-7.51 (m, 5H, aromatic), 7.59-7.69 (m, 2H, aromatic), 8.51 (s, 1H, NH). MS (CI, CH4): 367(M+1).

후처리

  1. customthe mixture (a precipitate formed after a few minutes)
  2. stirringto stir at room temperature overnight
  3. extractionextracted with ethyl ether (2×100 mL)
  4. dry with materialthe etheral extracts dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customThe residue was chromatographed on 315 g of silica gel using a ethyl ether (0%, 10%, and 20%) in methylene chloride gradient
  8. customthe solvent removed in vacuo
  9. dissolutionthe residue dissolved in a mixture of 100 mL hexane and 150 mL methylene chloride
  10. distillationMost of the methylene chloride was distilled off as the solution
  11. temperatureAfter cooling the solid
  12. customwas collected
  13. customdried at 85° C. /0.1 mm

출처 및 근거

ORD 기록
ord-49436b304a874002adb72b38f04a28eb
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05272163

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