Thiobenzamide → methyl 2-(5-methyl-2-phenyl-1,3-thiazol-4-yl)acetate

HRID 2300590ノート

反応式

HRID 2300590 の反応式
[C:1]([NH2:9])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH:11]([CH3:19])[C:12](=O)[CH2:13][C:14]([O:16][CH3:17])=[O:15].CCOC(C)=O.O>C1(C)C=CC=CC=1>[CH3:17][O:16][C:14](=[O:15])[CH2:13][C:12]1[N:9]=[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[S:8][C:11]=1[CH3:19]

参加物

5

反応物 3

HCID 683563ThiobenzamideHCID 9815681Methyl 4-bromo-3-oxopentanoateHCID 22728543Water ethylacetate

生成物 1

HCID 2775646methyl 2-(5-methyl-2-phenyl-1,3-thiazol-4-yl)acetate

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of 13.13 g (95.7 mmol) of thiobenzamide and 5.0 g (23.9 mmol) of methyl 4-bromo-3-oxo-pentanoate in 25 mL of dry toluene was heated at 90° C. for 5 h. The solution was poured into EtOAc/water and the aqueous phase extracted with EtOAc. The organics were washed with brine, dried (MgSO4), filtered, and concentrated. The crude oil was purified by silica gel chromatography eluting with hexanes/EtOAc (3/1 to 2/1) to afford 4.14 g (70%) yield) of the title compound as a pale orange-colored oil: 1H NMR (CDCl3, 400 MHz) δ7.97 (m, 2H), 7.11 (m, 2H), 3.73 (s, 3H), 3.56 (s, 2H), 2.36 (s, 3H).

後処理

  1. extractionthe aqueous phase extracted with EtOAc
  2. washThe organics were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude oil was purified by silica gel chromatography
  7. washeluting with hexanes/EtOAc (3/1 to 2/1)
  8. customto afford 4.14 g (70%)

出典と根拠

ORDレコード
ord-cf0ac6c23b46432bb0488c8f91d5af47
出典データセット
uspto-grants-2002_12
特許番号
US06498174B1

反応ノート

読み込み中…