2-Aminophenol → 4-Fluoro-N-(2-hydroxyphenyl)benzamide

HRID 59636

반응식

HRID 59636 반응식
C[C@H]1CO[C@@]2(O[C@H]3C[C@H]4[C@@H]5CC=C6C[C@@H](O)CC[C@]6(C)[C@H]5CC[C@]4(C)[C@H]3[C@@H]2C)CC1.C(=O)(O)[O-].[Na+].[NH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[OH:43].[F:44][C:45]1[CH:53]=[CH:52][C:48]([C:49](Cl)=[O:50])=[CH:47][CH:46]=1.CC1CCCO1>O>[F:44][C:45]1[CH:53]=[CH:52][C:48]([C:49]([NH:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[OH:43])=[O:50])=[CH:47][CH:46]=1

참가 물질

7

반응물 5

HCID 58012-Aminophenol2회HCID 73012-MethyltetrahydrofuranHCID 678794-Fluorobenzoyl chlorideHCID 99474DiosgeninHCID 516892Sodium Bicarbonate

생성물 1

HCID 5793834-Fluoro-N-(2-hydroxyphenyl)benzamide

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

To a 500 ml 4 necked round bottom flask equipped with a thermometer, a mechanic stirrer, a drop funnel, a nitrogen in-let, was added sodium bicarbonate (29.6 g, 0.354 mol, 1.1 eq), 2-aminophenol (34.88 g, 0.32 mol, 1 eq) and 2-Methyl THF (250 ml). The temperature of the mixture was controlled under 20° C. by ice-bath. Under vigorously stirring, 4-fluorobenzoyl chloride (50.72 g, 0.32 mol, 1 eq) was added drop wise within 10 min. Then the reaction was allowed to be stirred for another 1.5 hrs. When HPLC data showed that less than 0.3% of 2-aminophenol remained, 100 ml of water and 50 ml of 2-methyl tetrahydrofuran was added to quench the reaction and then the mixture was heated to 60° C. with stirring. The mixture was partitioned into two phases and the organic phase was washed with 100 ml of 1N H2SO4 and subsequently with 100 ml of water. Then the solvent was evaporated to almost dryness with stirring.

후처리

  1. customThe temperature of the mixture was controlled under 20° C. by ice-bath
  2. stirringto be stirred for another 1.5 hrs
  3. customto quench
  4. customthe reaction
  5. stirringwith stirring
  6. customThe mixture was partitioned into two phases
  7. washthe organic phase was washed with 100 ml of 1N H2SO4 and subsequently with 100 ml of water
  8. customThen the solvent was evaporated to almost dryness
  9. stirringwith stirring

출처 및 근거

ORD 기록
ord-184b04ec7f5642aabf0759c1f6f1a299
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440935B2

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