Acetic Acid → 4-Methyl-2,1,3-benzothiadiazol-5-amine

HRID 2110497ノート

反応式

HRID 2110497 の反応式
[CH3:1][C:2]1[C:7]2=[N:8][S:9][N:10]=[C:6]2[CH:5]=[CH:4][C:3]=1[N+:11]([O-])=O.C(O)(=O)C.O>C1COCC1.[Fe]>[CH3:1][C:2]1[C:7]2=[N:8][S:9][N:10]=[C:6]2[CH:5]=[CH:4][C:3]=1[NH2:11]

参加物

6

反応物 3

HCID 176Acetic AcidHCID 962WaterHCID 6764462,1,3-Benzothiadiazole, 4-methyl-5-nitro-

生成物 1

HCID 41871374-Methyl-2,1,3-benzothiadiazol-5-amine収率 92.7%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

4-Methyl-5-nitro-benzo[1,2,5]thiadiazole (1.4 g, 7.18 mmol) was dissolved in THF (10 mL), acetic acid (1 mL) and water (21 mL) and iron powder (1.4 g, 25.0 mmol, 325 Mesh) was added. The reaction mixture was heated at 80° C. for 1.5 h, cooled to rt and filtered though celite to remove the iron powder. The solution was extracted with CHCl3 (2×250 mL). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to give compound 839C (1.1 g) as a light brown solid.

後処理

  1. temperaturecooled to rt
  2. filtrationfiltered though celite
  3. customto remove the iron powder
  4. extractionThe solution was extracted with CHCl3 (2×250 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-ca96d3e8ca28494aae34dab7f57eb4f6
出典データセット
uspto-grants-2009_04
特許番号
US07517904B2

反応ノート

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