Dimethylamine → HCID 59442004, compound

HRID 1014386Notes

Reaction equation

HRID 1014386 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

HCID 59442004HCID 59442004, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-5429ec0cd98242bc9498e5b1bfe348de
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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