1,3-Propanediamine, N1,N1,N3-trimethyl- → HCID 16109013, compound

HRID 1361590Notes

Reaction equation

HRID 1361590 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](F)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[CH3:12][N:13]([CH3:19])[CH2:14][CH2:15][CH2:16][NH:17][CH3:18]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:17]([CH3:18])[CH2:16][CH2:15][CH2:14][N:13]([CH3:19])[CH3:12])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

3

Reactant 2

HCID 783021,3-Propanediamine, N1,N1,N3-trimethyl-HCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Product 1

HCID 16109013HCID 16109013, compound

Procedure

To a round bottom flask at 0° C. was added 4-Bromo-1-fluoro-2-nitrobenzene (10 g, 45 mmol) and N,N,N′-Trimethyl-propane-1,3-diamine (6.99 ml, 47.7 mmol). The reaction was allowed to warm to RT and stirred for 16 h. The reaction was extracted into EtOAc, washed once with saturated aqueous NaHCO3, twice with water, and then dried over Mg2SO4. The organic layer was filtered and concentrated to yield the title compound as a bright orange solid. MS (M+H+)=316, 318; Calc'd for C12H18BrN3O2=316.19.

Workup

  1. extractionThe reaction was extracted into EtOAc
  2. washwashed once with saturated aqueous NaHCO3, twice with water
  3. dry with materialdried over Mg2SO4
  4. filtrationThe organic layer was filtered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2d184d7b66034a8bad9dc616145a9219
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

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