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

HRID 1532336노트

반응식

HRID 1532336 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-997b2fb74a634b4a85737170112cfbc5
출처 데이터셋
uspto-grants-2001_03
특허 번호
US06201024B1

반응 노트

불러오는 중…