Water → N-(5-chloro-4-methyl-pyridin-2-yl)-2,2-dimethyl-propionamide

HRID 2374158노트

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HRID 2374158 반응식
[CH3:1][C:2]([CH3:14])([CH3:13])[C:3]([NH:5][C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][N:7]=1)=[O:4].O.C(Cl)[Cl:17]>>[Cl:17][C:9]1[C:10]([CH3:12])=[CH:11][C:6]([NH:5][C:3](=[O:4])[C:2]([CH3:14])([CH3:13])[CH3:1])=[N:7][CH:8]=1

참가 물질

4

반응물 3

HCID 962WaterHCID 6344DichloromethaneHCID 35314852,2-Dimethyl-N-(4-Methyl-2-pyridyl)propionamide

생성물 1

HCID 44597499N-(5-chloro-4-methyl-pyridin-2-yl)-2,2-dimethyl-propionamide

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온도
0 °C

실험 절차

2,2-Dimethyl-N-(4-methyl-pyridin-2-yl)-propionamide (42 g, 0.22 mol) from Step 1 was placed in a 3-neck 3 L flask fitted with an overhead stirrer. To this was added water (650 mL), then Na2HPO4 (78 g, 0.55 mol), followed by DCM (220 mL). The mixture was stirred and cooled in an ice-bath to 0° C., then chlorine gas was bubbled slowly through a sparge-frit. The reaction was monitored by TLC (EtOAc/hexanes 1/1), and found to be complete after 80 min. The reaction mixture was poured into a separatory funnel and extracted. The aqueous layer was re-extracted with DCM (2×100 mL). The combined layers were dried over Na2SO4 and concentrated to a crude solid product which was recrystallized from hexanes to yield the purified N-(5-chloro-4-methyl-pyridin-2-yl)-2,2-dimethyl-propionamide (41 g, 0.18 mol). 1H NMR (CDCl3) δ 8.18 (s, 1 H), 8.12 (s, 1 H), 7.94 (br s, 1 H), 2.35 (s, 3H), 1.29 (s, 9H).

후처리

  1. customfitted with an overhead stirrer
  2. customchlorine gas was bubbled slowly through a sparge-frit
  3. additionThe reaction mixture was poured into a separatory funnel
  4. extractionextracted
  5. extractionThe aqueous layer was re-extracted with DCM (2×100 mL)
  6. dry with materialThe combined layers were dried over Na2SO4
  7. concentrationconcentrated to a crude solid product which
  8. customwas recrystallized from hexanes

출처 및 근거

ORD 기록
ord-8c046c18eb7d40ffbcb8a544b382586c
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07462600B2

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