2-Methyl-5-nitrobenzene-1-sulfonamide → 5-Amino-2-[(E)-2-(4-amino-2-(aminosulfonyl)phenyl)ethenyl]benzenesulfonamide

HRID 277585

反応式

HRID 277585 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[S:11]([NH2:14])(=[O:13])=[O:12].[OH2:15].[OH2:16].[Sn](Cl)(Cl)(Cl)Cl>C(OCC)(=O)C>[NH2:8][C:5]1[CH:6]=[CH:7][C:2](/[CH:1]=[CH:1]/[C:2]2[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=2[S:11]([NH2:14])(=[O:16])=[O:15])=[C:3]([S:11]([NH2:14])(=[O:13])=[O:12])[CH:4]=1

参加物

4

反応物 2

HCID 2342822-Methyl-5-nitrobenzene-1-sulfonamideHCID 85782573Tin tetrachloride dihydrate

生成物 1

HCID 226290435-Amino-2-[(E)-2-(4-amino-2-(aminosulfonyl)phenyl)ethenyl]benzenesulfonamide収率 61.2%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒2 回

実験手順

In a round bottom flask under nitrogen was placed 5-nNitro-2-[(E)-2-(4-nitro-2-(aminosulfonyl)phenyl)ethenyl]benzenesulfonamide (Example 51, 0.38 g, 0.887 mmol) and 40 mL of ethyl acetate added. To this mixture was added tin chloride dihydrate (1.00 g, 4.44 mmol) and a reflux condenser was attached. The solution was heated in an oil bath to 80 C. and stirred for 16 hours. After cooling to room temperature the solution was diluted with ethyl acetate (250 mL) and washed with saturated sodium bicarbonate. The whole mixture was filtered thru Celite and the aqueous layer discarded. The organics were then washed with brine, dried (MgSO4) and concentrated on a rotovap to dryness. The crude material was then recrystallized from 10% methanol/dichloromethane and dried under vacuum to afford 100 mg of the title compound as a dark yellow solid (31%): 1HNMR (DMSO-d6) δ7.58 (d, J=8.5 Hz, 2H), 7.49 (s, 2H), 7.31 (br s, 4H), 7.15 (d, J=2 Hz, 2H), 6.75 (dd, J=8.5 Hz, 2 Hz, 2H), 5.65 (br s, 4H).

後処理

  1. customIn a round bottom flask under nitrogen was placed
  2. temperatureThe solution was heated in an oil bath to 80 C
  3. washwashed with saturated sodium bicarbonate
  4. filtrationThe whole mixture was filtered thru Celite
  5. washThe organics were then washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated on a rotovap to dryness
  8. customThe crude material was then recrystallized from 10% methanol/dichloromethane
  9. customdried under vacuum

出典と根拠

ORDレコード
ord-877411ef0d2e41b3804a6393dd79a102
出典データセット
uspto-grants-2002_03
特許番号
US06355633B1

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