Chloral Hydrate → 4-methyl-N-(2,2,2-trichloro-1-hydroxyethyl)benzamide

HRID 479489

반응식

HRID 479489 반응식
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([C:7]([NH2:9])=[O:8])=[CH:3][CH:2]=1.[Cl:11][C:12]([Cl:17])([Cl:16])[CH:13](O)[OH:14]>C1C=CC=CC=1.C(OCC)(=O)C>[CH3:10][C:1]1[CH:6]=[CH:5][C:4]([C:7]([NH:9][CH:13]([OH:14])[C:12]([Cl:17])([Cl:16])[Cl:11])=[O:8])=[CH:3][CH:2]=1

참가 물질

5

반응물 2

HCID 2707Chloral HydrateHCID 692744-Methylbenzamide

생성물 1

HCID 33926644-methyl-N-(2,2,2-trichloro-1-hydroxyethyl)benzamide수율 87.9%

시약·촉매·용매 2

HCID 241Benzene용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of p-toluamide (11.0 g, 81.3 mmol) and 2,2,2-trichloro-1,1-ethanediol (16.6 g, 100 mmol) in benzene (175 mL) was stirred at reflux in a Soxhlet extraction device charged with molecular sieves (20 g). After 12 hours, the extraction thimble of molecular sieves was replaced with a fresh portion of molecular sieves (20 g), and the reaction was allowed to heat at reflux for an additional 12 hours. Concentration in vacuo provided a heavy syrup which was dissolved in ethyl acetate (15 mL) and diluted with hexanes (175 mL). Refrigeration at 8° C. facilitated precipitation of a white solid that was collected by filtration and washed with hexanes to provide 20.2 g of the desired product.

후처리

  1. temperatureat reflux in a Soxhlet extraction device
  2. additioncharged with molecular sieves (20 g)
  3. temperatureto heat
  4. temperatureat reflux for an additional 12 hours
  5. concentrationConcentration in vacuo
  6. customprovided a heavy syrup which
  7. customat 8° C.
  8. customprecipitation of a white solid
  9. filtrationthat was collected by filtration
  10. washwashed with hexanes

출처 및 근거

ORD 기록
ord-d4687b689ecf42e2b13ad5d623b9ae5e
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06645968B2

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