Chloroacetyl chloride → Acetamide, N-(5-hydroxy-1-naphthalenyl)-

HRID 395225

반응식

HRID 395225 반응식
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[OH:12].C(=O)([O-])[O-].[Ca+2].Cl[CH2:19][C:20](Cl)=[O:21]>O1CCOCC1>[OH:12][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]2[C:8]=1[CH:9]=[CH:10][CH:11]=[C:2]2[NH:1][C:20](=[O:21])[CH3:19]

참가 물질

5

반응물 3

HCID 6577Chloroacetyl chlorideHCID 10112Calcium CarbonateHCID 657465-Amino-1-naphthol

생성물 1

HCID 89653Acetamide, N-(5-hydroxy-1-naphthalenyl)-수율 76%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
80 °C

실험 절차

To a solution of 5-amino-1-naphthol (17.6 g; 0.11 mol) in 500 ml of dioxane, there were added 11 g of calcium carbonate (0.11 mol) and, dropwise, 8 ml of chloroacetyl chloride (0.112 mol), with stirring and under an inert atmosphere. The reaction medium was heated at 80° C. for 2 hours 30 minutes. The suspension was cooled to room temperature, filtered on sintered glass and the inorganic salts were rinsed twice with dioxane. The mixture of the organic solutions was concentrated until an insoluble product appeared, and then poured over 400 ml of ice-cold water. The precipitate formed was drained, washed once with water and once with pentane. The brown powder obtained was dried under vacuum to a constant weight to give 16.8 g of N-(5-hydroxynaphthalen-1-yl)acetamide with a yield of 76%.

후처리

  1. temperatureThe suspension was cooled to room temperature
  2. filtrationfiltered on sintered glass
  3. washthe inorganic salts were rinsed twice with dioxane
  4. additionThe mixture of the organic solutions
  5. concentrationwas concentrated until an insoluble product
  6. additionpoured over 400 ml of ice-cold water
  7. customThe precipitate formed
  8. washwashed once with water and once with pentane
  9. customThe brown powder obtained
  10. customwas dried under vacuum to a constant weight

출처 및 근거

ORD 기록
ord-55fcf9a0869941169b9bf0431bf74234
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06605124B1

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