Thionicotinamide → 4-(2-Hydroxyphenyl)-2-(3-pyridyl)thiazole

HRID 366438

反応式

HRID 366438 の反応式
C([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11](=O)[CH2:12]Br)(=O)C.[C:15]([NH2:23])(=[S:22])[C:16]1[CH:21]=[CH:20][CH:19]=[N:18][CH:17]=1>CC(C)=O>[N:18]1[CH:19]=[CH:20][CH:21]=[C:16]([C:15]2[S:22][CH:12]=[C:11]([C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[OH:4])[N:23]=2)[CH:17]=1

参加物

4

反応物 2

HCID 737155ThionicotinamideHCID 12956296o-(Bromoacetyl)phenyl acetate

生成物 1

HCID 232893034-(2-Hydroxyphenyl)-2-(3-pyridyl)thiazole収率 36%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
20 °C

実験手順

o-(Bromoacetyl)phenyl acetate (2.57 g, 10 mmol) in dry acetone (30 mL) was treated with thionicotinamide (1.38 g, 10 mmol). The mixture was refluxed 16 hours, cooled to about 20° C. at which point a precipitate formed (2.46 g). The precipitate was filtered and dried in vacuo. The precipitate was dissolved in MeOH (50 mL) and treated with 10% NaOH in H2O (20 mL) for 1 hour at about 20° C. to hydrolyze the acetate ester. The pH was adjusted to neutrality with 6N HCl while chilling on ice/H2O and the volume was reduced to about 35 mL in vacuo. After cooling to about 4° C., an orange solid precipitate formed, which was removed by filtration and dried in vacuo to constant mass to yield 36-50% product (LSIMS m/s 254 (MH+)).

後処理

  1. temperatureThe mixture was refluxed 16 hours
  2. customformed (2.46 g)
  3. filtrationThe precipitate was filtered
  4. customdried in vacuo
  5. dissolutionThe precipitate was dissolved in MeOH (50 mL)
  6. additiontreated with 10% NaOH in H2O (20 mL) for 1 hour at about 20° C.
  7. temperaturewhile chilling on ice/H2O
  8. temperatureAfter cooling to about 4° C.
  9. customan orange solid precipitate formed
  10. customwhich was removed by filtration
  11. customdried in vacuo to constant mass

出典と根拠

ORDレコード
ord-2df6a646106e4179ad26bb85ef0ba612
出典データセット
uspto-grants-2000_10
特許番号
US06130217

関連ノート

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