Dimethylamine → HCID 59442004, 화합물

HRID 1014386노트

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HRID 1014386 반응식
[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]

참가 물질

7

반응물 4

HCID 674Dimethylamine2회HCID 11430Potassium CarbonateHCID 89602Bromoacetyl chlorideHCID 145678141208091-01-3

생성물 1

HCID 59442004HCID 59442004, 화합물수율 64%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매3회HCID 8857Ethyl Acetate용매

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온도
50 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5429ec0cd98242bc9498e5b1bfe348de
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981903B2

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