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ノート

反応式

HRID 1158958 の反応式
[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]

参加物

7

反応物 4

HCID 111,2-DichloroethaneHCID 74034-tert-Butylbenzoic acidHCID 516892Sodium BicarbonateHCID 12332441HCID 12332441、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bf3ab3193be14c4da456ea2c04d3bfd6
出典データセット
uspto-grants-2010_10
特許番号
US07812037B2

反応ノート

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