Sodium Azide → Ethyl 5-azido-4,5,6,7-tetrahydro-3-methylthio-4-oxobenzo(c]thiophene-1-carboxylate

HRID 1066209ノート

反応式

HRID 1066209 の反応式
Br[CH:2]1[CH2:17][CH2:16][C:5]2=[C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[S:7][C:8]([S:9][CH3:10])=[C:4]2[C:3]1=[O:18].[N-:19]=[N+:20]=[N-:21].[Na+]>CN(C)C=O.O>[N:19]([CH:2]1[CH2:17][CH2:16][C:5]2=[C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[S:7][C:8]([S:9][CH3:10])=[C:4]2[C:3]1=[O:18])=[N+:20]=[N-:21]

参加物

5

反応物 2

HCID 33557Sodium AzideHCID 15885619Ethyl 5-bromo-4,5,6,7-tetrahydro-3-methylthio-4-oxobenzo[c]thiophene-1-carboxylate

生成物 1

HCID 18388306Ethyl 5-azido-4,5,6,7-tetrahydro-3-methylthio-4-oxobenzo(c]thiophene-1-carboxylate収率 80.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒

実験手順

Ethyl 5-bromo-4,5,6,7-tetrahydro-3-methylthio-4-oxobenzo[c]thiophene-1-carboxylate (5.24 g) was suspended in N,N-dimethylformamide (80 ml); a solution of sodium azide (1.95 g) in water (12 ml) was added at 0° C. After the reaction mixture was stirred at room temperature for 4 hours, it was poured over water (50 ml) and extracted with ethyl acetate. The organic layer was washed with water and dried (MgSO4), after which the solvent was distilled off. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:9 to 1:2, v/v) to yield ethyl 5-azido-4,5,6,7-tetrahydro-3-methylthio-4-oxobenzo[c]thiophene-1-carboxylate (3.77 g, 80.7%), which was then recrystallized from ethyl acetate-hexane. Colorless needles. Melting point 163-164° C. (decomposed).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried (MgSO4)
  4. distillationafter which the solvent was distilled off
  5. washeluted with ethyl acetate-hexane (1:9 to 1:2

出典と根拠

ORDレコード
ord-9f2194a57e6e4fc683fa077bfe1fb913
出典データセット
uspto-grants-2001_06
特許番号
US06242471B1

反応ノート

読み込み中…