Dimethylamine → HCID 24973049, compound

HRID 1966438Notes

Reaction equation

HRID 1966438 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:15]([O-:17])=[O:16])=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=1.[CH3:18][NH:19][CH3:20].O1CCCC1>CN1C(=O)CCC1>[CH3:18][N:19]([CH3:20])[C:2]1[CH:3]=[CH:4][C:5]([N+:15]([O-:17])=[O:16])=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 2386965-bromo-2-nitro-n-phenylaniline

Product 1

HCID 24973049HCID 24973049, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 5-bromo-2-nitro-N-phenylbenzenamine (0.2 g, 0.68 mmol) and 2.0 M dimethylamine in tetrahydrofuran (1.3 ml, 2.7 mmol) in 10 ml NMP was heated at 100° C. for 16 hours. The reaction was quenched with 100 ml water. The mixture was extracted with ethyl acetate (3×30 ml) and dried over anhydrous sodium sulfate. N1,N1-dimethyl-4-nitro-N3-phenylbenzene-1,3-diamine (0.17 g, 100%) was obtained by flash column chromatograph (30% ethyl acetate in hexanes). 1H NMR (500 MHz, CDCl3) δ (ppm) 3.02 (s, 6H), 6.21 (d, J=2.6 Hz, 1H), 6.23 (s, 1H), 7.22-7.45 (m, 5H), 8.17 (d, J=2.6 Hz, 1H), 9.96 (s, 1H). 13C NMR (125 MHz, CDCl3): δ (ppm) 40.5, 93.6, 104.8, 124.9, 125.4, 129.5, 130.0, 139.8, 145.9, 155.5.

Workup

  1. customThe reaction was quenched with 100 ml water
  2. extractionThe mixture was extracted with ethyl acetate (3×30 ml)
  3. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-21d8c291167449d191ca88765c050ff3
Source dataset
uspto-grants-2013_04
Patent number
US08420640B2

Reaction notes

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