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

HRID 1715227

반응식

HRID 1715227 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e4a20fd958ac43b19eea5d4ea87e7ca1
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07799814B2

연결된 노트

불러오는 중…