Thionyl Chloride → 2-Bromoimidazo[2,1-b]thiazole-6-carbonyl azide

HRID 716509ノート

反応式

HRID 716509 の反応式
S(Cl)(Cl)=O.[Br:5][C:6]1[S:10][C:9]2=[N:11][C:12]([C:14]([OH:16])=O)=[CH:13][N:8]2[CH:7]=1.[N-:17]=[N+:18]=[N-:19].[Na+]>O>[Br:5][C:6]1[S:10][C:9]2=[N:11][C:12]([C:14]([N:17]=[N+:18]=[N-:19])=[O:16])=[CH:13][N:8]2[CH:7]=1

参加物

5

反応物 3

HCID 24386Thionyl ChlorideHCID 33557Sodium AzideHCID 127446152-Bromoimidazo[2,1-b]thiazole-6-carboxylic acid

生成物 1

HCID 583102352-Bromoimidazo[2,1-b]thiazole-6-carbonyl azide収率 80%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
85 °C

実験手順

Thionyl chloride (0.33 mol) was added to 2-bromoimidazo[2,1-b]thiazole-6-carboxylic acid (13.1 mmol). The reaction mixture was stirred at 85° C. during 3 hrs. The mixture was then concentrated under vacuum and the residue was taken in acetone (40 mL). The sodium azide (14.4 mmol) in water (5.2 mL) was added in one portion at 0° C. and the mixture was stirred at 0-10° C. for 45 min. Water was added, and the solid filtered off and washed with water and then with a mixture of water/acetone (50/50). The solid was dried in vacuo to give compound 9 as a beige solid in 80% yield. 1H NMR (DMSO-d6, 400 MHz) δ (ppm) 8.27 (s, 1H), 8.49 (s, 1H); and MS (ESI, EI+) m/z=272.05-274.07 (MH+).

後処理

  1. concentrationThe mixture was then concentrated under vacuum
  2. stirringthe mixture was stirred at 0-10° C. for 45 min
  3. filtrationthe solid filtered off
  4. washwashed with water
  5. additionwith a mixture of water/acetone (50/50)
  6. customThe solid was dried in vacuo

出典と根拠

ORDレコード
ord-8b634c5bef6842e691d610e4791aa1ed
出典データセット
uspto-grants-2015_11
特許番号
US09187496B2

反応ノート

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