Dichloromethane → Ethyl 2-(bromomethyl)-1,3-thiazole-4-carboxylate

HRID 489226

반응식

HRID 489226 반응식
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([CH3:11])[S:9][CH:10]=1)=[O:5])[CH3:2].[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)Cl>ClCCCl>[Br:12][CH2:11][C:8]1[S:9][CH:10]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[N:7]=1

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 293353Ethyl 2-methyl-1,3-thiazole-4-carboxylate

생성물 1

HCID 11043146Ethyl 2-(bromomethyl)-1,3-thiazole-4-carboxylate수율 8%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

반응 조건

온도
70 °C

실험 절차

A mixture of ethyl-2-methylthiazole 4-carboxylate (500 mg, 2.9 mmol), N-bromosuccinimide (877 mg, 4.9 mmol), and benzoyl peroxide (5-10 mg ) in 1,2-DCE (3 mL) was heated at 70° C. for 85 h. After cooling to room temperature, DCM (10 ml) was added and washed with water (3 times). The organic layer was dried over Na2SO4 and evaporated in vacuo. The residue was purified by preparative chromatography to yield the above-titled compound (58 mg). 1H NMR (CDCl3): 8.23 (1H, s), 4.77 (2H, s), 4.43 (2H, q), 1.42 (3H, t).

후처리

  1. temperatureAfter cooling to room temperature
  2. washwashed with water (3 times)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customevaporated in vacuo
  5. customThe residue was purified by preparative chromatography

출처 및 근거

ORD 기록
ord-93c2e3cc1941461180df679fb132fe9a
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06977267B2

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