1,5-Diazabicyclo(4.3.0)non-5-ene → N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine

HRID 1042341

反応式

HRID 1042341 の反応式
[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.C1CN2C(=NCCC2)C1.[Br:25][C:26]1[S:27][CH:28]=[C:29]([CH:31](Br)C)[N:30]=1>CC#N>[Br:25][C:26]1[S:27][CH:28]=[C:29]([CH2:31][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:30]=1

参加物

5

反応物 3

HCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 668607482-Bromo-4-(1-bromoethyl)-1,3-thiazoleHCID 135990939N-hydroxy-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine

生成物 1

HCID 86649974N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine収率 568.6%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
0 °C

実験手順

To a cooled (0° C.) stirred solution of N-hydroxy-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (0.7 g, 3.44 mmol, 1.0 eq.) in 25 ml of MeCN, was added dropwise DBN (0.42 g, 3.44 mmol, 1.0 eq.). The reaction was stirred for 5 mins before addition of 2-bromo-4-(1-bromoethyl)-1,3-thiazole (0.86 g, 3.2 mmol, 0.93 eq.) portionwise. The mixture was stirred for further 5 mins before removal of the cooling bath and continued at ambient temperature. LCMS after 2 h would indicate reaction complete. MeCN was evaporated and the residue was purified by chromatography on silica gel to yield N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (6.9 g, 79% yield, 9:1 mixture of stereoisomers).

後処理

  1. customcontinued at ambient temperature
  2. waitLCMS after 2 h would indicate
  3. customreaction complete
  4. customMeCN was evaporated
  5. customthe residue was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-263d67cf9e924700af90064f0277fc34
出典データセット
uspto-grants-2013_10
特許番号
US08557849B2

関連ノート

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