Bromine → N-[5-(bromoacetyl)-4-methyl-1,3-thiazol-2-yl]acetamide, hydrobromide salt

HRID 1715227

反応式

HRID 1715227 の反応式
[Br:1]Br.[C:3]([C:6]1[S:10][C:9]([NH:11][C:12](=[O:14])[CH3:13])=[N:8][C:7]=1[CH3:15])(=[O:5])[CH3:4]>O1CCOCC1>[BrH:1].[Br:1][CH2:4][C:3]([C:6]1[S:10][C:9]([NH:11][C:12](=[O:14])[CH3:13])=[N:8][C:7]=1[CH3:15])=[O:5]

参加物

4

反応物 2

HCID 24408BromineHCID 830648N-(5-acetyl-4-methyl-1,3-thiazol-2-yl)acetamide

生成物 1

HCID 87942046N-[5-(bromoacetyl)-4-methyl-1,3-thiazol-2-yl]acetamide, hydrobromide salt収率 60%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒2 回

反応条件

温度
50 °C

実験手順

A solution of Br2 (3.35 ml, 65.6 mmol) in 75 ml dioxane is added dropwise to a solution of N-(5-acetyl-4-methyl-1,3-thiazol-2-yl)acetamide (P6), obtained in Step I as described above, (10.40 g, 52.5 mmol) in 200 ml dioxane. The resulting mixture is heated at 50° C. for 19 hours. The solution turns from dark red to beige and remains a heterogeneous mixture. By analytical HPLC, only 2.8% of starting material is detected. The suspension is filtered, washed with a 1:2 EtOAc/hexanes mixture (50 ml) and air dried for 15 min, to give Intermediate 1 as a beige solid (11.2 g, 60%). It is used in bis-thiazol synthesis as HBr salt or as parent, after 5 min treatment with Amberlyst A21 in DCM/MeOH mixture.

後処理

  1. customobtained in Step I
  2. filtrationThe suspension is filtered
  3. washwashed with a 1:2 EtOAc/hexanes mixture (50 ml) and air
  4. customdried for 15 min

出典と根拠

ORDレコード
ord-e4a20fd958ac43b19eea5d4ea87e7ca1
出典データセット
uspto-grants-2010_09
特許番号
US07799814B2

関連ノート

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