Iodoethane → (4-Bromo-2-tert-butylphenyl)diethylamine

HRID 1158147노트

반응식

HRID 1158147 반응식
[H-].[Na+].[Br:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=1.[CH2:15](I)[CH3:16].[Cl-].[NH4+].O1CC[CH2:22][CH2:21]1>CS(C)=O>[Br:3][C:4]1[CH:10]=[CH:9][C:7]([N:8]([CH2:15][CH3:16])[CH2:21][CH3:22])=[C:6]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=1

참가 물질

7

반응물 5

HCID 6340IodoethaneHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 119590004-bromo-2-tert-butylphenylamine

생성물 1

HCID 66671963(4-Bromo-2-tert-butylphenyl)diethylamine수율 91%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

6.9 g (0.17 mol) of sodium hydride are suspended in 200 mL of tetrahydrofuran. 13 g (57 mmol) of 4-bromo-2-tert-butylaniline are added, along with 200 mL of dimethyl sulfoxide, added slowly. The mixture turns blue and, after 30 minutes, 13 mL (0.17 mol) of ethyl iodide are added and the reaction medium, which has turned white, is stirred at room temperature for 13 hours. The reaction medium is then poured into saturated ammonium chloride solution and extracted with ethyl acetate, and the organic phase is then washed twice with water. It is dried and then concentrated to dryness. The residue is purified by chromatography on silica gel (eluent: 90/10 heptane/ethyl acetate). 14.8 g of (4-bromo-2-tert-butylphenyl)diethylamine are obtained (yield=91%) in the form of a yellow oil.

후처리

  1. additionadded slowly
  2. extractionextracted with ethyl acetate
  3. washthe organic phase is then washed twice with water
  4. customIt is dried
  5. concentrationconcentrated to dryness
  6. customThe residue is purified by chromatography on silica gel (eluent: 90/10 heptane/ethyl acetate)

출처 및 근거

ORD 기록
ord-a839151c14c7491892e272a0e0e70ade
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807708B2

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