Sulfuric Acid → 2,3,4,5-tetrahydro-1H-1-benzazepine-2,5-dione

HRID 235288

反応式

HRID 235288 の反応式
OS(O)(=O)=O.[C:6]1(=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[CH:8]=[CH:7]1.[N-:18]=[N+]=[N-].[Na+]>>[NH:18]1[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9](=[O:16])[CH2:8][CH2:7][C:6]1=[O:17]

参加物

4

反応物 3

HCID 1118Sulfuric AcidHCID 85301,4-NaphthoquinoneHCID 33557Sodium Azide

生成物 1

HCID 3693982,3,4,5-tetrahydro-1H-1-benzazepine-2,5-dione収率 84.9%

実験手順

To 10 mL of H2SO4 (97% ) cooled in an ice-bath was added portionwise 1.08 g (6.86 mmol) of 1,4-naphthoquinone and it was stirred to become a solution. To the red solution was added portionwise 0.454 g (6.98 mmol) of NaN3. The mixture was stirred in ice bath for 2 h, then at room temperature for 2 days. It was added dropwise into 100 mL of ice-water and stirred for 1 h and allowed to stand overnight. The mixture was filtered and washed thoroughly by water, dried to leave brown solid 1.02 g. 1H NMR (CDCl3 +DMSO-d6) shows it is more than 80% pure. Portion of the solid was crystallized (DMSO/H2O) to give 32 as a brown solid, mp 225°-226° C. 1H NMR (CDCl3 +DMSO-d6) 6.544 (d, 1, J=12.9), 6.657 (d, 1, J=12.9), 6.978 (t, 1, J=7.5), 7.152 (d, 1, J=8.4), 7.323 (t, 1, J=7.5), 7.812 (d, 1, J=8.1), 10.55 (bs, 1).

後処理

  1. stirringThe mixture was stirred in ice bath for 2 h
  2. stirringstirred for 1 h
  3. waitto stand overnight
  4. filtrationThe mixture was filtered
  5. washwashed thoroughly by water
  6. customdried

出典と根拠

ORDレコード
ord-246f882eb20443c8ad5f73736fe9164a
出典データセット
uspto-grants-1997_01
特許番号
US05597922

関連ノート

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