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

HRID 2038362노트

반응식

HRID 2038362 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 24380Iron chloride (FeCl3)촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ce04511ec4f045cbb03e025b3bdae732
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575357B2

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