Dichloromethane → HCID 15683606, compound

HRID 1458714Notes

Reaction equation

HRID 1458714 reaction equation
C(N(CC)CC)C.[CH3:8][N:9]([CH2:11][CH2:12][NH:13][C:14](=[O:31])[C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=1[N:24]([CH2:28]CO)[CH2:25][CH2:26]O)[CH3:10].S([Cl:36])(C)(=O)=O.[CH2:37]([Cl:39])Cl>>[CH3:8][N:9]([CH2:11][CH2:12][NH:13][C:14](=[O:31])[C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=1[N:24]([CH2:28][CH2:37][Cl:39])[CH2:25][CH2:26][Cl:36])[CH3:10]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 15683605HCID 15683605, compound

Product 1

HCID 15683606HCID 15683606, compound

Procedure

Triethylamine (4.5 ml; 32 mmol) was added to a solution of 2.6 g (0.76 mmol) of N-[(N,N-dimethylamino)ethyl]-2-[N,N-bis(2-hydroxyethyl)amino]-5-nitrobenzamide in 20 ml of methylene chloride, followed by cooling over an ice bath. The thus-obtained solution was added with 1.8 ml (23 mmol) of mesyl chloride, followed by stirring at room temperature for 3 hours. After the reaction mixture was washed with a saturated aqueous solution of sodium hydrogencarbonate, magnesium sulfate was added to the organic layer to dry the same. The solvent was distilled out under reduced pressure. The residue was dissolved in 10 ml of DMF, to which 5 g of sodium chloride were added. The resulting mixture was then stirred at 150° C. for 30 minutes. After the thus-obtained mixture was cooled to room temperature, the sodium chloride was filtered off and the solvent was distilled out under reduced pressure. The residue was purified by chromatography on a silica gel column (chloroform/methanol=10/1), whereby 0.95 g of the title compound was obtained as yellow powder (yield: 33%).

Workup

  1. temperatureby cooling over an ice bath
  2. washAfter the reaction mixture was washed with a saturated aqueous solution of sodium hydrogencarbonate, magnesium sulfate
  3. additionwas added to the organic layer
  4. customto dry the same
  5. distillationThe solvent was distilled out under reduced pressure
  6. dissolutionThe residue was dissolved in 10 ml of DMF, to which 5 g of sodium chloride
  7. additionwere added
  8. stirringThe resulting mixture was then stirred at 150° C. for 30 minutes
  9. temperatureAfter the thus-obtained mixture was cooled to room temperature
  10. filtrationthe sodium chloride was filtered off
  11. distillationthe solvent was distilled out under reduced pressure
  12. customThe residue was purified by chromatography on a silica gel column (chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-0b6c980f39524964865cc7aaaf112a51
Source dataset
uspto-grants-1998_12
Patent number
US05852011

Reaction notes

Loading…