Dimethylamine → HCID 59442004、化合物

HRID 1014386ノート

反応式

HRID 1014386 の反応式
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH3:11].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20](Cl)=[O:21].[CH3:23][NH:24][CH3:25]>O1CCCC1.C(OCC)(=O)C>[CH3:1][N:2]([C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH3:11])[C:20](=[O:21])[CH2:19][N:24]([CH3:25])[CH3:23]

参加物

7

反応物 4

HCID 674Dimethylamine2 回HCID 11430Potassium CarbonateHCID 89602Bromoacetyl chlorideHCID 145678141208091-01-3

生成物 1

HCID 59442004HCID 59442004、化合物収率 64%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒3 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

A suspension of N,2-dimethyl-4-(methyloxy)aniline (5.10 g, 33.7 mmol) and potassium carbonate (9.32 g, 67.5 mmol) in tetrahydrofuran (150 ml) was treated with bromoacetylchloride (3.50 ml, 42.2 mmol), stirred for 45 minutes, and dimethyl amine in tetrahydrofuran (67.5 ml, 135 mmol) was added. The solution was stirred for 3 hours, additional dimethyl amine in tetrahydrofuran (67.5 ml, 135 mmol) was added, and the solution was warmed to 50° C. and maintained overnight. The solution was cooled, poured into ethyl acetate/saturated sodium bicarbonate, and the organic layer was separated, dried over sodium sulfate, filtered, taken to a residue under reduced pressure, and purified by column chromatography to afford N1,N2,N2-trimethyl-N1-[2-methyl-4-(methyloxy)phenyl]glycinamide (5.10 g, 21.58 mmol, 64.0% yield) as a yellow oil. 1H NMR (400 MHz, DMSO-d6); two protons likely obstructed by DMSO; δ ppm 7.13 (d, J=8.6 Hz, 1 H), 6.90 (d, J=2.6 Hz, 1 H), 6.77-6.84 (m, 1 H), 3.76 (s, 3 H), 3.00 (s, 3 H), 2.13 (s, 3 H), 2.08 (s, 6 H).

後処理

  1. stirringThe solution was stirred for 3 hours
  2. temperaturemaintained overnight
  3. temperatureThe solution was cooled
  4. customthe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. custompurified by column chromatography

出典と根拠

ORDレコード
ord-5429ec0cd98242bc9498e5b1bfe348de
出典データセット
uspto-grants-2011_07
特許番号
US07981903B2

反応ノート

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