Potassium Carbonate → N'-(2,3-dimethyl-benzoyl)-hydrazinecarboxylic acid, tert-butyl ester

HRID 39644

반응식

HRID 39644 반응식
[C:1]([O:5][C:6](=[O:9])[NH:7][NH2:8])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH3:16][C:17]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:18]=1[C:19](Cl)=[O:20]>O.C(Cl)Cl>[CH3:16][C:17]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:18]=1[C:19]([NH:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:9])=[O:20]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 70091tert-Butyl carbazateHCID 28008992,3-Dimethylbenzoyl chloride

생성물 1

HCID 59838585N'-(2,3-dimethyl-benzoyl)-hydrazinecarboxylic acid, tert-butyl ester수율 101.7%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

T-butylcarbazate (35.15 g, 266 mmol) and 200 mL of CH2Cl2 were added to a round bottom flask. Potassium carbonate (55.2 g, 0.4 moles) dissolved in 350 mL of water was added to the flask, and the mixture was stirred for 15 minutes with ice chilling. 2,3 dimethylbenzoyl chloride (44.9 g, 266 mmol) in ca. 200 mL of CH2Cl2 was added drop-wise from a 500 mL separatory funnel over 30 minutes. The reaction was allowed to stir overnight and then the reaction mixture was poured into a 1 L separatory funnel and the CH2Cl2 phase was separated. Then ca. 150 mL of water was added, and the mixture was extracted twice with 150 mL of CHCl3. The combined organic phase was back-extracted with 100 mL of water, then with 1N HCl (250 mL), to remove the hydrazide. The organic phase was dried, stirred with charcoal, and the solvent removed in vacuo to yield a light tan solid (71.5 g) of N′-(2,3-dimethyl-benzoyl)-hydrazinecarboxylic acid, tert-butyl ester. 1H NMR (300 MHz, CHCl3) δ (ppm): 7.7 (br, 1H), 7.22 (m, 2H), 7.1 (t, 1H), 7.85 (br, 1H), 2.35 (s, 3H), 2.3 (s, 3H), 1.5 (s, 9H).

후처리

  1. additionwas added to the flask
  2. stirringto stir overnight
  3. additionthe reaction mixture was poured into a 1 L separatory funnel
  4. customthe CH2Cl2 phase was separated
  5. additionThen ca. 150 mL of water was added
  6. extractionthe mixture was extracted twice with 150 mL of CHCl3
  7. extractionThe combined organic phase was back-extracted with 100 mL of water
  8. customwith 1N HCl (250 mL), to remove the hydrazide
  9. customThe organic phase was dried
  10. stirringstirred with charcoal
  11. customthe solvent removed in vacuo

출처 및 근거

ORD 기록
ord-ea03b90d93ed4c0a84c66ad41fddd115
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524948B2

연결된 노트

불러오는 중…