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

HRID 1258572ノート

反応式

HRID 1258572 の反応式
[CH3:1][N:2]1[C:6]([C:7](=[N:14][O:15][CH2:16][C:17]2[N:18]=[C:19](N)[S:20][CH:21]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:5][N:4]=[N:3]1.[Br-:23].[Na+].C(ON=O)(C)(C)C>CC#N.[Cu]Br>[Br:23][C:19]1[S:20][CH:21]=[C:17]([CH2:16][O:15][N:14]=[C:7]([C:6]2[N:2]([CH3:1])[N:3]=[N:4][N:5]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:18]=1

参加物

6

反応物 3

HCID 10906Tert-Butyl nitriteHCID 253881Sodium BromideHCID 866531284-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]-1,3-thiazol-2-amine

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 73%

試薬・触媒・溶媒 2

HCID 24593copper(I) bromide触媒HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

To a stirred suspension of 4-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]-1,3-thiazol-2-amine (41 g, 130 mmol, 1 eq.) in 2000 ml of MeCN, were added sodium bromide (40.1 g, 390 mmol, 3 eq.), Copper (I) bromide (18.65 g, 130 mmol, 1 eq.) and t-Butylnitrite (16.38 g, 143 mmol, 1.1 eq.). The reaction was slowly heated to 80° C. for 1 h and allowed to cool. MeCN was evaporated and 500 ml water/1000 ml DCM were added to the residue. The crude was triturated, filtered through “celite” plug and washed with further 500 ml of EtOAc. The organic layers were combined, dried over MgSO4, and evaporated to give N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (36 g, 69% yield, 10:1 mixture of stereoisomers) as a brown viscous oil.

後処理

  1. temperatureto cool
  2. customMeCN was evaporated
  3. addition500 ml water/1000 ml DCM were added to the residue
  4. customThe crude was triturated
  5. filtrationfiltered through “celite” plug
  6. washwashed with further 500 ml of EtOAc
  7. dry with materialdried over MgSO4
  8. customevaporated

出典と根拠

ORDレコード
ord-ff3bd57991c84d639ed842c2ab947573
出典データセット
uspto-grants-2013_06
特許番号
US08466176B2

反応ノート

読み込み中…