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

HRID 59636

反応式

HRID 59636 の反応式
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

参加物

7

反応物 5

HCID 58012-Aminophenol2 回HCID 73012-MethyltetrahydrofuranHCID 678794-Fluorobenzoyl chlorideHCID 99474DiosgeninHCID 516892Sodium Bicarbonate

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-184b04ec7f5642aabf0759c1f6f1a299
出典データセット
uspto-grants-2016_09
特許番号
US09440935B2

関連ノート

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