1,2-Dichloroethane → 4-tert-Butyl-N-(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl-methyl)-benzamide

HRID 1158958

반응식

HRID 1158958 반응식
[CH3:1][C:2]1([CH3:15])[O:14][C:6]2=[C:7]([CH3:13])[N:8]=[CH:9][C:10]([CH2:11][NH2:12])=[C:5]2[CH2:4][O:3]1.[C:16]([C:20]1[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17].C(Cl)CCl.C(=O)(O)[O-].[Na+]>CN(C1C=CN=CC=1)C.ClCCl>[C:16]([C:20]1[CH:21]=[CH:22][C:23]([C:24]([NH:12][CH2:11][C:10]2[CH:9]=[N:8][C:7]([CH3:13])=[C:6]3[O:14][C:2]([CH3:15])([CH3:1])[O:3][CH2:4][C:5]=23)=[O:25])=[CH:27][CH:28]=1)([CH3:19])([CH3:17])[CH3:18]

참가 물질

7

반응물 4

HCID 111,2-DichloroethaneHCID 74034-tert-Butylbenzoic acidHCID 516892Sodium BicarbonateHCID 12332441HCID 12332441, 화합물

생성물 1

HCID 586368334-tert-Butyl-N-(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl-methyl)-benzamide수율 86.3%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

A mixture of C-(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)-methylamine (1.77 g, 8.49 mmol), 4-tert-butylbenzoic acid (5.6 g, 31 mmol), EDC (5.7 g, 29 mmol), and DMAP (4.53 g, 35.6 mmol) was stirred in dichloromethane (200 mL) for 24 hours. Saturated aqueous sodium bicarbonate was added to the reaction mixture, and the dichloromethane layer was separated. The aqueous layer was then extracted with dichloromethane. The combined organic layer was dried over anhydrous magnesium sulfate, filtered and evaporated. The crude mixture was purified by column chromatography on silica gel using a gradient mixture of dichloromethane:acetone (1:0 to 7:3) as eluant to give 4-tert-butyl-N-(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl-methyl)-benzamide (74) (2.7 g, 85%) as a light yellow solid.

후처리

  1. customthe dichloromethane layer was separated
  2. extractionThe aqueous layer was then extracted with dichloromethane
  3. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude mixture was purified by column chromatography on silica gel using
  7. additiona gradient mixture of dichloromethane:acetone (1:0 to 7:3) as eluant

출처 및 근거

ORD 기록
ord-bf3ab3193be14c4da456ea2c04d3bfd6
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812037B2

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