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

HRID 489226

反応式

HRID 489226 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

反応条件

温度
70 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-93c2e3cc1941461180df679fb132fe9a
出典データセット
uspto-grants-2005_12
特許番号
US06977267B2

関連ノート

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