Dimethylamine → N2,N2-dimethyl-N1-[2-methyl-4-(methyloxy)-5-nitrophenyl]glycinamide

HRID 1014405Notes

Reaction equation

HRID 1014405 reaction equation
Cl.[CH3:2][C:3]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([N+:12]([O-:14])=[O:13])=[CH:6][C:4]=1[NH2:5].[CH3:15][CH2:16][N:17]([CH:21](C)C)[CH:18](C)C.BrCC(Cl)=[O:27].CNC>C1COCC1.CCOC(C)=O>[CH3:18][N:17]([CH3:21])[CH2:16][C:15]([NH:5][C:4]1[CH:6]=[C:7]([N+:12]([O-:14])=[O:13])[C:8]([O:10][CH3:11])=[CH:9][C:3]=1[CH3:2])=[O:27]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 89602Bromoacetyl chlorideHCID 673166642-methyl-4-(methyloxy)-5-nitroaniline HCl salt

Product 1

HCID 59441880N2,N2-dimethyl-N1-[2-methyl-4-(methyloxy)-5-nitrophenyl]glycinamideYield 104.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-methyl-4-(methyloxy)-5-nitroaniline HCl salt (500 mg, 2.287 mmol) and Hunig's Base (1.198 ml, 6.86 mmol) was stirred in THF (20 ml). Bromoacetyl chloride (0.211 ml, 2.52 mmol) was added and the reaction let stir at rt for 40 min. LCMS analysis indicated complete conversion to the acyl bromide so a 2M solution of dimethylamine in THF (4.6 ml, 9.15 mmol) was added and let stir at rt overnight. The reaction was diluted with EtOAc and washed with a saturated brine solution. Aqueous layers were re-extracted with EtOAc. Organics were combined and dried over sodium sulfate and filtered. Solvents were removed under reduced pressure to afford N2,N2-dimethyl-N1-[2-methyl-4-(methyloxy)-5-nitrophenyl]glycinamide (0.642 mg, 2.4 mmol). ESIMS (M+H)+=268.

Workup

  1. additionwas added
  2. stirringlet stir at rt overnight
  3. washwashed with a saturated brine solution
  4. extractionAqueous layers were re-extracted with EtOAc
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customSolvents were removed under reduced pressure

Sources & evidence

ORD record
ord-39da42e6c1f748aa92cace4c230bfbbe
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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