Nitrogen → HCID 86664759, 화합물

HRID 1044779

반응식

HRID 1044779 반응식
N#N.Cl[CH2:4][C:5]1[N:6]=[C:7]([C:10](=[O:12])[CH3:11])[S:8][CH:9]=1.[N-:13]=[N+:14]=[N-:15].[Na+]>CN(C=O)C>[N:13]([CH2:4][C:5]1[N:6]=[C:7]([C:10](=[O:12])[CH3:11])[S:8][CH:9]=1)=[N+:14]=[N-:15]

참가 물질

5

반응물 3

HCID 947NitrogenHCID 33557Sodium AzideHCID 668199771-(4-Chloromethyl-thiazol-2-yl)ethanone

생성물 1

HCID 86664759HCID 86664759, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 1-(4-chloromethyl-thiazol-2-yl)-ethanone (1.08 g, 6.13 mmol) in dry DMF (21 mL) and treated with NaN3 (1.20 g, 18.39 mmol) at 65° C. until completion of the reaction. The reaction mixture was then cooled down to rt and partitioned between EA and water. The layers were separated and the org. layer dried over MgSO4, filtered and concentrated under reduced pressure to give crude 1-(4-(azidomethyl)-thiazol-2-yl)-ethanone as a yellow oil. To a solution of the crude azide (200 mg, 1.10 mmol) in THF (6 mL) were added polymer-supported Ph3P (2.0 eq.) and water (2 mL). The reaction mixture was stirred at 60° C. until completion of the reaction, cooled down to rt and filtered. The filtrate was partitioned between EA and aq. sat. NaHCO3 and the layers separated. The org. layer was dried over MgSO4, filtered and concentrated under reduced pressure to give the title compound as a brown oil after purification by FC (CH2Cl2-MeOH-Et3N). LC-MS-conditions 01: tR=0.26 min; [M+H]+=157.04.

후처리

  1. custompartitioned between EA and water
  2. customThe layers were separated
  3. dry with materiallayer dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-f36e7442c31e4460b6918ebd8b5fd132
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08563714B2

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