Ethyl bromoacetate → Ethyl [5-(5-bromo-1,3,4-thiadiazol-2-yl)-2H-tetrazol-2-yl]acetate

HRID 1753967노트

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HRID 1753967 반응식
[Br:1][C:2]1[S:6][C:5]([C:7]2[NH:11][N:10]=[N:9][N:8]=2)=[N:4][N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>CN(C=O)C>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][N:10]1[N:9]=[N:8][C:7]([C:5]2[S:6][C:2]([Br:1])=[N:3][N:4]=2)=[N:11]1)[CH3:24]

참가 물질

5

반응물 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 1784194815-(5-bromo-1,3,4-thiadiazol-2-yl)-1H-tetrazole

생성물 1

HCID 59321687Ethyl [5-(5-bromo-1,3,4-thiadiazol-2-yl)-2H-tetrazol-2-yl]acetate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
90 °C

실험 절차

To a solution of 5-(5-bromo-1,3,4-thiadiazol-2-yl)-1H-tetrazole (1 g, 4.3 mmol) in DMF (20 mL) was added Cs2CO3 (2.1 g, 6.45 mmol) and ethyl bromoacetate (0.95 mL, 8.6 mmol). The resulting solution was stirred at 90° C. for 1 hour. The mixture was partitioned between EtOAc (100 mL) and water (200 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and evaporated in vacuo. Chromatography over silica afforded the title compound as a white solid, contaminated with the 1-alkylated isomer ethyl[5-(5-bromo-1,3,4-thiadiazol-2-yl)-1H-tetrazol-1-yl]acetate. 1HNMR (CDCl3, 300 MHz): δ 5.70 (s, 2H), 4.26 (q, J=7 Hz, 2H), 1.28 (t, J=7 Hz, 3H).

후처리

  1. customThe mixture was partitioned between EtOAc (100 mL) and water (200 mL)
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-27b25af02aca4891b361acb7153f18be
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09168248B2

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