P-Anisidine → 7-Methoxy-2H-benzo[e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxide

HRID 30984

反応式

HRID 30984 の反応式
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[CH3:8][O:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1.[Cl-].[Al+3].[Cl-].[Cl-]>[N+](CC)([O-])=O>[CH3:8][O:9][C:10]1[CH:16]=[CH:15][C:13]2[NH:14][C:6](=[O:7])[NH:5][S:2](=[O:4])(=[O:3])[C:12]=2[CH:11]=1

参加物

5

反応物 3

HCID 7732P-AnisidineHCID 70918Chlorosulfonyl isocyanateHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 125284907-Methoxy-2H-benzo[e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxide収率 95%

試薬・触媒・溶媒 1

HCID 6587Nitroethane溶媒2 回

反応条件

温度
-40 °C

実験手順

A solution of chlorosulfonyl isocyanate (17 mL, 195 mmol.) was dissolved in 150 mL of nitroethane and cooled to −40° C. A solution of 4-methoxyaniline (Z) (20 g, 162 mmol) in 100 mL of nitroethane was then added drop-wise from a dropper funnel with stirring. After the addition was completed, the reaction was stirred for an additional 5 minutes and aluminum chloride (25 g, 195 mmol) was added. The mixture was then quickly heated to 110° C. with stirring for 20 minutes. The crude material was then poured onto ice and the precipitate was collected by suction filtration, washed with cold water, and dried in vacuo to produce 35 g of the desired product (8) as a purple powder in 95% yield. 1H NMR (400 MHz, DMSO-d6): δ 11.05 (s, 1H), 7.2 (m, 3H), 3.78 (s, 3H), 3.6 (br, 1H).

後処理

  1. additionAfter the addition
  2. stirringthe reaction was stirred for an additional 5 minutes
  3. temperatureThe mixture was then quickly heated to 110° C.
  4. stirringwith stirring for 20 minutes
  5. filtrationthe precipitate was collected by suction filtration
  6. washwashed with cold water
  7. customdried in vacuo

出典と根拠

ORDレコード
ord-6983da0e423f4f0586daf65b5c99150f
出典データセット
uspto-grants-2008_09
特許番号
US07425552B2

関連ノート

読み込み中…