Methanesulfonic Acid → HCID 23025824、化合物

HRID 1437462ノート

反応式

HRID 1437462 の反応式
P(Cl)(Cl)(Cl)(Cl)Cl.CS(O)(=O)=O.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:14]=1[OH:20].[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29](O)=O)=[CH:24][CH:23]=1.[OH-].[Na+]>>[Br:19][C:16]1[CH:17]=[CH:18][C:13]2[N:12]=[C:29]([CH2:28][C:25]3[CH:26]=[CH:27][C:22]([Cl:21])=[CH:23][CH:24]=3)[O:20][C:14]=2[CH:15]=1

参加物

6

反応物 5

HCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 15880(4-Chlorophenyl)acetic acidHCID 24819Phosphorus pentachlorideHCID 143206052-Amino-5-bromophenol

生成物 1

HCID 23025824HCID 23025824、化合物収率 71.2%

反応条件

温度
120 °C

実験手順

Phosphorus pentachloride (2.27 g) was added to methanesulfonic acid (8 ml), and the mixture was stirred at 120° C. for 1 hour. To the solution were added 2-amino-5-bromophenol (1.50 g) and 4-chlorophenylacetic acid (1.36 g) and the mixture was stirred at 100° C. for 1 hour. The mixture was poured onto ice, neutralized with 8 N sodium hydroxide and extracted with ethyl acetate-tetrahydrofuran (3:1, v/v). The organic layer was washed with water and dried over MgSO4. The solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography and the fraction eluted with ethyl acetate-hexane (1:4, v/v) was concentrated under reduced pressure. The resulting crystals were collected by filtration to obtain 6-bromo-2-(4-chlorobenzyl)benzoxazole (1.83 g, 71%).

後処理

  1. stirringthe mixture was stirred at 100° C. for 1 hour
  2. additionThe mixture was poured onto ice
  3. extractionextracted with ethyl acetate-tetrahydrofuran (3:1
  4. washThe organic layer was washed with water
  5. dry with materialdried over MgSO4
  6. distillationThe solvent was distilled off under reduced pressure
  7. washthe fraction eluted with ethyl acetate-hexane (1:4, v/v)
  8. concentrationwas concentrated under reduced pressure
  9. filtrationThe resulting crystals were collected by filtration

出典と根拠

ORDレコード
ord-b8d3043ab83f4c54a68fb11450ea06d7
出典データセット
uspto-grants-2009_11
特許番号
US07622479B2

反応ノート

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