3,5-Dinitrobenzoyl chloride → HCID 22797306, compound

HRID 2397354Notes

Reaction equation

HRID 2397354 reaction equation
[CH3:1][NH:2][CH2:3][C@@H:4]([C@H:6]([C@@H:8]([C@@H:10]([CH2:12][OH:13])[OH:11])[OH:9])[OH:7])[OH:5].C(N(CC)CC)C.[N+:21]([C:24]1[CH:25]=[C:26]([CH:30]=[C:31]([N+:33]([O-:35])=[O:34])[CH:32]=1)[C:27](Cl)=[O:28])([O-:23])=[O:22]>CN(C=O)C.O1CCOCC1>[N+:21]([C:24]1[CH:25]=[C:26]([CH:30]=[C:31]([N+:33]([O-:35])=[O:34])[CH:32]=1)[C:27]([N:2]([CH3:1])[CH2:3][C@@H:4]([C@H:6]([C@@H:8]([C@@H:10]([CH2:12][OH:13])[OH:11])[OH:9])[OH:7])[OH:5])=[O:28])([O-:23])=[O:22]

Participants

6

Reactant 3

HCID 74323,5-Dinitrobenzoyl chlorideHCID 8471TriethylamineHCID 8567N-Methyl-D-glucamine

Product 1

HCID 22797306HCID 22797306, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

N-Methylglucamine (21.4 g, 0.11 mol) was suspended in DMF (200 ml). Triethylamine (11.5 g, 0.11 mol) was added. To this suspension was at 4° added by stirring 3,5-dinitrobenzoyl chloride (23.0 g, 0.1 mol) dissolved in dioxane (100 ml). The temperature rose to 10°. The stirring was continued at this temperature for 2 hours followed by 16 hours at room temperature. Triethylamine hydrochloride was filtered off and the DMF distilled off from the filtrate. The residue, a pale brown oil, was dissolved in water (200 ml), the pH adjusted to 1 and the solution extracted with phenol according to standard procedure. The final aqueous solution was treated with charcoal at room temperature for 24 hours and the filtrate evaporated to dryness in vacuo. The residue -- a pale brown oil -- was further dried in vacuo at 65°. Yield: 25.5 g (65%). The IR-spectrum showed a characteristic carbonyl absorption band at 1670 -- 1620 cm -1. Rf value: 0.55 - 0.6 (paper, n-BuOH: EtOH: NH3 : H2O= 4 : 1 : 2 : 1).

Workup

  1. customwas at 4°
  2. additionadded
  3. customrose to 10°
  4. waitfollowed by 16 hours at room temperature
  5. filtrationTriethylamine hydrochloride was filtered off
  6. distillationthe DMF distilled off from the filtrate
  7. dissolutionThe residue, a pale brown oil, was dissolved in water (200 ml)
  8. extractionthe solution extracted with phenol according to standard procedure
  9. additionThe final aqueous solution was treated with charcoal at room temperature for 24 hours
  10. customthe filtrate evaporated to dryness in vacuo
  11. customThe residue -- a pale brown oil -- was further dried in vacuo at 65°
  12. customa characteristic carbonyl absorption band at 1670

Sources & evidence

ORD record
ord-3f94e8b0d43849009050e34f7ab7a5c9
Source dataset
uspto-grants-1977_05
Patent number
US04021481

Reaction notes

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