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

HRID 1110218Notes

Reaction equation

HRID 1110218 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].[CH2:16]([NH2:26])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].C([N:29]([CH2:32][CH3:33])CC)C.O1[CH2:38][CH2:37][CH2:36][CH2:35]1>S(Cl)(Cl)=O.O.CN(C=O)C>[CH2:16]([NH:26][C:9]([C:8]1[CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[C:6]([C:13]([NH:29][CH2:32][CH2:33][CH2:35][CH2:36][CH2:37][CH2:38][CH2:5][CH2:4][CH2:12][CH3:8])=[O:15])[CH:7]=1)=[O:11])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 8916DecylamineHCID 120695-Nitroisophthalic acid

Product 1

HCID 19388993N,N'-didecyl-5-nitro-1,3-benzenedicarboxamideYield 150.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 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 residue acid chloride was dissolved in 220 ml of anhydrous tetrahydrofuran. This solution was added dropwise to 64 ml (0.32 mol) of decyl amine and 44 ml (0.32 mol) of triethylamine in 350 mol 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 residue 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-877bba8994ec41448896d18659791015
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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