Dimethylformamide → N,N'-didecyl-5-nitro-1,3-benzenedicarboxamide

HRID 1757779Notes

Reaction equation

HRID 1757779 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:13]([OH:15])=O)[CH:7]=[C:8]([CH:12]=1)[C:9]([OH:11])=O)([O-:3])=[O:2].C[N:17]([CH:19]=O)C.[CH2:21]([NH2:31])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].C(N([CH2:37][CH3:38])CC)C>S(Cl)(Cl)=O.O1CCCC1.O>[CH2:21]([NH:31][C:9]([C:8]1[CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[C:6]([C:13]([NH:17][CH2:19][CH2:7][CH2:6][CH2:5][CH2:4][CH2:12][CH2:8][CH2:9][CH2:37][CH3:38])=[O:15])[CH:7]=1)=[O:11])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 8916DecylamineHCID 120695-Nitroisophthalic acid

Product 1

HCID 19388993N,N'-didecyl-5-nitro-1,3-benzenedicarboxamideYield 74%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 24386Thionyl ChlorideSolvent

Procedure

To 30 g (0.14 mol) of 5-nitroisophthalic acid suspended in 120 ml of thionyl chloride was added 2 ml of DMF and the solution was stirred at reflux for 3.5 hours. The excess thionyl chloride was removed at reduced pressure and the residual acid chloride was dissolved in 220 ml of anhydrous tetrahydrofuran. This solution was added dropwise to 64 ml (0.32mol) of decyl amine and 44 ml (0.32 mol) of triethylamine in 350 ml of anhydrous tetrahydrofuran over 30 minutes with ice bath cooling. The reaction mixture was stirred at room temperature for 4 hours and then poured into 3 L of water. The resultant solid was removed by filtration and recrystallized from methanol to give 51.5 g (74% yield, mp 115°-116°) of N,N'-didecyl-5-nitro-1,3-benzenedicarboxamide.

Workup

  1. temperatureat reflux for 3.5 hours
  2. customThe excess thionyl chloride was removed at reduced pressure
  3. dissolutionthe residual acid chloride was dissolved in 220 ml of anhydrous tetrahydrofuran
  4. temperaturecooling
  5. stirringThe reaction mixture was stirred at room temperature for 4 hours
  6. customThe resultant solid was removed by filtration
  7. customrecrystallized from methanol

Sources & evidence

ORD record
ord-58e8780dd70c4d5295fb23e3bbdb6667
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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