Triethylamine → HCID 59441965, compound

HRID 1014223Notes

Reaction equation

HRID 1014223 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6](N)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].C([N:14](CC)CC)C.CN(C1C=CC=CN=1)C.Cl.[CH3:29][N:30]([CH2:32][C:33](Cl)=[O:34])[CH3:31].C(=O)(O)[O-].[Na+]>ClCCl>[CH3:29][N:30]([CH3:31])[CH2:32][C:33]([NH:14][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1)=[O:34]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 118984-Nitro-m-toluidineHCID 218852-DimethylaminopyridineHCID 516892Sodium BicarbonateHCID 139949912-(Dimethylamino)acetyl chloride hydrochloride2×

Product 1

HCID 59441965HCID 59441965, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methyl-4-amino nitro benzene (5.00 g, 32.3 mmol) in dichloromethane (200 mL) was added triethylamine (12 mL, 97 mmol, 3 equiv.), dimethylaminopyridine (ca 500 mg) and dimethylaminoacetyl chloride hydrochloride (6.50 g, 41.1 mmol, 1.25 equiv.). The resulting clear solution was stirred 24 hours, at which time additional dimethylaminoacetyl chloride hydrochloride (1.50 g, 9.5 mmol, 0.30 equiv.) was added. After an additional 24 hrs. the reaction was poured into saturated aqueous sodium bicarbonate. The organic layer was dried over sodium sulfate, taken to a residue under reduced pressure, and purified by chromatography on SiO2 (0 to 10% methonal/CH2CL2) to give N2,N2-dimethyl-N1-(4-methyl-3-nitrophenyl)glycinamide (7.0 g, 29.5 mmol, 91% yield) as a brown oil. 1H NMR (400 MHz, CDCl3) δ ppm 2.40 (s, 6 H), 2.55 (s, 3 H), 3.11 (s, 2 H), 7.28 (d, J=8.42 Hz, 1H), 7.86 (dd, J=8.32, 2.29 Hz, 1 H), 8.15 (d, J=2.38 Hz, 1 H), 9.33 (s, 1 H),

Workup

  1. additionwas added
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. custompurified by chromatography on SiO2 (0 to 10% methonal/CH2CL2)

Sources & evidence

ORD record
ord-e861a87f926e4ea2946b7466bf462726
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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