Triethylamine → HCID 10791062, compound

HRID 503681Notes

Reaction equation

HRID 503681 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH2:21][CH2:22][OH:23])[C:5]1[C:6]([N+:18]([O-:20])=[O:19])=[C:7]([C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=1)[C:8]([O:10][CH3:11])=[O:9].CCN(CC)CC.[CH3:31][S:32](Cl)(=[O:34])=[O:33].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:31][S:32]([O:1][CH2:2][CH2:3][N:4]([CH2:21][CH2:22][O:23][S:32]([CH3:31])(=[O:34])=[O:33])[C:5]1[C:6]([N+:18]([O-:20])=[O:19])=[C:7]([C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])(=[O:34])=[O:33]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 10664096HCID 10664096, compound

Product 1

HCID 10791062HCID 10791062, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 3-[bis(2-hydroxyethyl)amino]-2,6-dinitrobenzoate [Palmer et al., J. Med. Chem. 1996, 39, 2518] (7.24 g, 22 mmol) in CH2Cl2 (120 mL) was cooled in an ice-bath and Et3N (15 mL) and MsCl (8 mL) were added in one portion. After stirred for 10 min, satd. NaHCO3 (100 mL) was added, and after a further 30 min the aqueous phase was extracted with CH2Cl2 (2×70 mL), the combined organic phase were dried, concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel. Elution with EtOAc/petroleum ether (1:1 to 1:0), gave crude methyl 3-(bis{2-[(methylsulfonyl)oxy]ethyl}amino)-2,6-dinitrobenzoate (16) (10.67 g, 100%) as a yellow oil;

Workup

  1. extractionafter a further 30 min the aqueous phase was extracted with CH2Cl2 (2×70 mL)
  2. customthe combined organic phase were dried
  3. concentrationconcentrated under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel
  5. washElution with EtOAc/petroleum ether (1:1 to 1:0)

Sources & evidence

ORD record
ord-ff978230dfc34c4180f71245d4f60ce8
Source dataset
uspto-grants-2010_08
Patent number
US07776924B2

Reaction notes

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