Triethylamine → 2-methyl-N-[(4-methylphenyl)methyl]benzamide

HRID 915359

반응식

HRID 915359 반응식
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21]>C(Cl)Cl>[CH3:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([NH:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([CH3:1])=[CH:3][CH:4]=1)=[O:21]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 660354-MethylbenzylamineHCID 702762-Methylbenzoyl chloride

생성물 1

HCID 8354792-methyl-N-[(4-methylphenyl)methyl]benzamide수율 85%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 4-methylbenzylamine (2.0 mL, 15.7 mmol), and triethylamine (4.4 mL, 31.6 mmol) in CH2Cl2 (50 mL) was cooled in an ice bath and treated dropwise with 2-methylbenzoyl chloride (2.5 mL, 19.2 mmol). After the end of the addition the ice bath was removed and the reaction mixture was allowed to warm to ambient temperature. After stirring at ambient temperature for 14 hours the resulting white suspension was diluted with CH2Cl2 (100 mL), and quenched by the addition of water (20 mL) and saturated aqueous sodium bicarbonate (20 mL). The aqueous layer was extracted with CH2Cl2 (3×30 mL), and the combined organics were dried over Na2SO4, filtered and concentrated to afford a white solid. The crude solid was recrystallized from ethyl acetate/hexane to afford 2-methyl-N-(4-methylbenzyl)benzamide (3.18 g, 85% yield) as a white crystalline solid: 1H-NMR (400 MHz, CDCl3): δ 7.36 (1H, dd, J=7.6, 1.3 Hz), 7.32-7.14 (7H, m), 5.98 (1H, br s), 4.59 (2H, d, J=5.6 Hz), 2.47 (3H, s), 2.35 (3H, s) ppm.

후처리

  1. customwas removed
  2. additionwas diluted with CH2Cl2 (100 mL)
  3. customquenched by the addition of water (20 mL) and saturated aqueous sodium bicarbonate (20 mL)
  4. extractionThe aqueous layer was extracted with CH2Cl2 (3×30 mL)
  5. dry with materialthe combined organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a white solid
  9. customThe crude solid was recrystallized from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-43ec7ae019a34efc871a9eecb8d2e0f4
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07265131B2

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