Triethylamine → HCID 86747961, compound

HRID 1110308Notes

Reaction equation

HRID 1110308 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]([C:13]([OH:15])=O)[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=O)([O-:3])=[O:2].S(Cl)(Cl)=O.[CH2:20]([NH2:30])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C([N:33]([CH2:36][CH3:37])CC)C>C1COCC1.O.CN(C=O)C>[CH2:20]([NH:30][C:6]([C:5]1[CH:9]=[CH:10][C:11]([C:13]([NH:33][CH2:36][CH2:37][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:15])=[CH:12][C:4]=1[N+:1]([O-:3])=[O:2])=[O:8])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8916DecylamineHCID 24386Thionyl ChlorideHCID 691221,4-Benzenedicarboxylic acid, 2-nitro-

Product 1

HCID 86747961HCID 86747961, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 10 g (0.047 mol) of nitroterephthalic acid, 40 ml of thionyl chloride and 1 ml of anhydrous DMF was stirred at reflux for 5 hours. The reaction mixture was concentrated at reduced pressure and the residual acid chloride was dissolved in anhydrous THF and added dropwise over 30 minutes to a stirred, ice bath cooled solution of 25 ml (0.126 mol) of decylamine and 15 ml (0.108 mol) of triethylamine in 100 ml of anhydrous THF. Additional THF (50 ml) was added and stirring was continued for 17 hours at room temperature. Water (1 L) was added and the precipitate was filtered and recrystallized from methanol-water to give 20.4 g, mp 159°-160° of N-[2,5-bis[(decylamino)carbonyl]nitrobenzene.

Workup

  1. temperatureat reflux for 5 hours
  2. concentrationThe reaction mixture was concentrated at reduced pressure
  3. dissolutionthe residual acid chloride was dissolved in anhydrous THF
  4. additionadded dropwise over 30 minutes to a stirred, ice bath
  5. stirringstirring
  6. filtrationthe precipitate was filtered
  7. customrecrystallized from methanol-water

Sources & evidence

ORD record
ord-a306068801e24b96904eccee9862a2a9
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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