Sulfuric Acid → 2-Chloro-5iodo-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

HRID 1532336ノート

反応式

HRID 1532336 の反応式
N[C:2]1[CH:3]=[CH:4][C:5]([Cl:22])=[C:6]([CH:21]=1)[C:7]([NH:9][CH2:10][C:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]3)[CH2:12]1)[CH2:18]2)=[O:8].S(=O)(=O)(O)O.N([O-])=O.[Na+].[I-:32].[K+]>O1CCCC1.O>[Cl:22][C:5]1[CH:4]=[CH:3][C:2]([I:32])=[CH:21][C:6]=1[C:7]([NH:9][CH2:10][C:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]3)[CH2:12]1)[CH2:18]2)=[O:8]

参加物

7

反応物 4

HCID 1118Sulfuric AcidHCID 4875Potassium IodideHCID 227314875-Amino-2-chloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamideHCID 23668193Sodium Nitrite

生成物 1

HCID 120853472-Chloro-5iodo-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide収率 85.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of amino amide from Example 55 (200 mg) in 75% aqueous tetrahydrofuran 1/3 (10 ml) at −5 C. was added sulphuric acid (0.2 ml) followed by sodium nitrite (0.042 g) in water (1 ml). The resulting reaction mixture was stirred for 40 min before potassium iodide (0.136 g) was added. The reaction mixture was heated at 90 C. for 1 hour, cooled to room temperature and diluted with water and extracted with ethyl acetate. The organic layers were separated and dried over magnesium sulphate. The filtered solution was concentrated under reduced pressure and the crude material purified over silica eluting with hexaneslethyl acetate to give the title compound as a white solid (0.23 g).

後処理

  1. customThe resulting reaction mixture
  2. additionwas added
  3. temperatureThe reaction mixture was heated at 90 C
  4. extractionextracted with ethyl acetate
  5. customThe organic layers were separated
  6. dry with materialdried over magnesium sulphate
  7. concentrationThe filtered solution was concentrated under reduced pressure
  8. customthe crude material purified over silica eluting with hexaneslethyl acetate

出典と根拠

ORDレコード
ord-997b2fb74a634b4a85737170112cfbc5
出典データセット
uspto-grants-2001_03
特許番号
US06201024B1

反応ノート

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