N-bromobutanimide → Methyl 2-[3-bromo-4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylate

HRID 1710782ノート

反応式

HRID 1710782 の反応式
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[S:13][C:14]([C:18]([O:20][CH3:21])=[O:19])=[C:15]([CH3:17])[N:16]=2)=[CH:8][CH:7]=1.[Br:22]N1C(=O)CCC1=O>C(#N)C>[Br:22][C:7]1[CH:8]=[C:9]([C:12]2[S:13][C:14]([C:18]([O:20][CH3:21])=[O:19])=[C:15]([CH3:17])[N:16]=2)[CH:10]=[CH:11][C:6]=1[O:5][CH2:4][CH2:3][CH2:2][Cl:1]

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 59457477Methyl 2-[4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylate

生成物 1

HCID 59457515Methyl 2-[3-bromo-4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylate収率 24%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

反応条件

温度
60 °C

実験手順

A solution of methyl 2-[4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylate ax60 (2 g, 6.15 mmol, 1 eq) in acetonitrile (50 ml) is treated with a solution of N-bromosuccinimide (1.8 g, 10 mmol, 1.5 eq) in acetonitrile (10 ml) and the resulting solution is stirred 2 h at room temperature and 2 h at 60° C. After cooling, the mixture is concentrated to dryness. The residue is taken up with ethyl acetate, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. Purification of the residue over silicagel (eluent: dichloromethane/benzine) affords 0.6 g of methyl 2-[3-bromo-4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylate i91.

後処理

  1. temperatureAfter cooling
  2. concentrationthe mixture is concentrated to dryness
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customPurification of the residue over silicagel (eluent: dichloromethane/benzine)

出典と根拠

ORDレコード
ord-c1f7d4a7954c4507ac4cf1102712b33f
出典データセット
uspto-grants-2010_09
特許番号
US07790720B2

反応ノート

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