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

HRID 716509노트

반응식

HRID 716509 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매2회

반응 조건

온도
85 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-8b634c5bef6842e691d610e4791aa1ed
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187496B2

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