N-bromobutanimide → Ethyl 5-bromo-4-(3-chloro-4-fluorophenyl)-1,3-thiazole-2-carboxylate

HRID 2038362ノート

反応式

HRID 2038362 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[S:12][CH:13]=2)[CH:5]=[CH:6][C:7]=1[F:8].[Br:19]N1C(=O)CCC1=O>ClCCl.[Fe](Cl)(Cl)Cl>[Br:19][C:13]1[S:12][C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:10][C:9]=1[C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Cl:1])[CH:3]=1

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 61385370Ethyl 4-(3-chloro-4-fluorophenyl)-1,3-thiazole-2-carboxylate

生成物 1

HCID 70801639Ethyl 5-bromo-4-(3-chloro-4-fluorophenyl)-1,3-thiazole-2-carboxylate

試薬・触媒・溶媒 2

HCID 24380Iron chloride (FeCl3)触媒HCID 6344Dichloromethane溶媒

実験手順

1.94 g of the compound from Example 2A having a purity of 57% (3.87 mmol) are provided in 35 ml of dichloromethane, 6.04 g (33.9 mmol) of N-bromosuccinimide and a spatula tip of iron trichloride are added and the mixture is heated under reflux for 18 hours. The reaction mixture is concentrated, the residue is purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 30:1), and 1.30 g (83% of theory) of the title compound are obtained.

後処理

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 18 hours
  3. concentrationThe reaction mixture is concentrated
  4. customthe residue is purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 30:1), and 1.30 g (83% of theory) of the title compound
  5. customare obtained

出典と根拠

ORDレコード
ord-ce04511ec4f045cbb03e025b3bdae732
出典データセット
uspto-grants-2013_11
特許番号
US08575357B2

反応ノート

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