Cesium carbonate → N-[(2-bromo-5-methyl-1,3-thiazol-4-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine

HRID 1258552노트

반응식

HRID 1258552 반응식
[OH:1][N:2]=[C:3]([C:10]1[N:14]([CH3:15])[N:13]=[N:12][N:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([O-])([O-])=O.[Cs+].[Cs+].[Br:22][C:23]1[S:24][C:25]([CH3:30])=[C:26]([CH2:28]Br)[N:27]=1>CC#N>[Br:22][C:23]1[S:24][C:25]([CH3:30])=[C:26]([CH2:28][O:1][N:2]=[C:3]([C:10]2[N:14]([CH3:15])[N:13]=[N:12][N:11]=2)[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:27]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 671901442-Bromo-4-(bromomethyl)-5-methyl-1,3-thiazoleHCID 135990939N-hydroxy-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine

생성물 1

HCID 86653110N-[(2-bromo-5-methyl-1,3-thiazol-4-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine수율 102.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a stirred solution of N-hydroxy-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (1.47 g, 7.25 mmol, 1.0 eq.) in 25 ml of MeCN was added Cs2CO3 (2.59 g, 7.97 mmol, 1.1 eq.) followed by KI (0.120 g, 0.725 mmol, 0.1 eq.) in one portion. The resulting suspension was stirred for 5 mins before addition of 2-bromo-4-(bromomethyl)-5-methyl-1,3-thiazole (1.96 g, 7.25 mmol, 1 eq.) in one portion. The reaction was stirred for 24 hrs at room temperature. The solvent was evaporated and the residue was dissolved in EtOAc and washed with H2O. The organic layer was separated, dried over MgSO4 and concentrated. The residue was purified by chromatography on silica gel to give N-[(2-bromo-5-methyl-1,3-thiazol-4-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (2.92 g, 97% yield, 93:7 mixture of stereoisomers) as a white solid.

후처리

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with H2O
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-e65563c291494475a758424e5d8810d2
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466176B2

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