Acetic Acid → N-acetyl-N-(5-amino-benzo[d]isothiazol-3-yl)-acetamide

HRID 1766301ノート

反応式

HRID 1766301 の反応式
[C:1]([N:4]([C:8]1[C:12]2[CH:13]=[C:14]([N+:17]([O-])=O)[CH:15]=[CH:16][C:11]=2[S:10][N:9]=1)[C:5](=[O:7])[CH3:6])(=[O:3])[CH3:2].C(O)(=O)C.C(=O)(O)[O-].[Na+]>[Fe].C(OCC)(=O)C>[C:1]([N:4]([C:8]1[C:12]2[CH:13]=[C:14]([NH2:17])[CH:15]=[CH:16][C:11]=2[S:10][N:9]=1)[C:5](=[O:7])[CH3:6])(=[O:3])[CH3:2]

参加物

6

反応物 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 21110339N-acetyl-N-(5-nitro-benzo[d]isothiazol-3-yl)-acetamide

生成物 1

HCID 21110338N-acetyl-N-(5-amino-benzo[d]isothiazol-3-yl)-acetamide収率 38%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

To a suspension of N-acetyl-N-(5-nitro-benzo[d]isothiazol-3-yl)-acetamide (1.133 g, 4.06 mmol) in a 1:1 acetic acid:ethyl acetate solution (70 mL) at 50° C. was added iron powder (680 mg, 12.2 mmol). The resulting mixture was stirred at 50° C. for 5 h, then cooled, poured into saturated sodium bicarbonate and extracted into ethyl acetate. The organic layers were combined, washed with water and then brine, dried (MgSO4), filtered, and evaporated. The residue was purified using flash chromatography on silica to afford the desired amine as an orange solid (383 mg, 38%), single spot at Rf 0.30 (1:1 dichloromethane:ethyl acetate). mp 213.0-214.2° C. 1H NMR (CDCl3): δ 8.56 (1H, d, J=9.2 Hz), 7.48 (d, J=2.7 Hz), 7.14 (1H, dd, J=9.2, 2.7 Hz), 2.62 (3H, s), 2.56 (3H, s).

後処理

  1. temperaturecooled
  2. extractionextracted into ethyl acetate
  3. washwashed with water
  4. dry with materialbrine, dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified

出典と根拠

ORDレコード
ord-32b750b3c32c410ab54be4422cf1fee4
出典データセット
uspto-grants-2007_06
特許番号
US07230020B2

反応ノート

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