Hydrochloric Acid → HCID 16115123, compound

HRID 503672Notes

Reaction equation

HRID 503672 reaction equation
[CH3:1][S:2]([O:5][CH2:6][CH2:7][N:8]([CH2:24][CH2:25][O:26][S:27]([CH3:30])(=[O:29])=[O:28])[C:9]1[C:10]([N+:21]([O-:23])=[O:22])=[CH:11][C:12]([N+:18]([O-:20])=[O:19])=[C:13]([CH:17]=1)[C:14]([OH:16])=O)(=[O:4])=[O:3].[NH2:31][CH2:32][CH2:33][OH:34].Cl>O=S(Cl)Cl.CN(C=O)C>[CH3:1][S:2]([O:5][CH2:6][CH2:7][N:8]([CH2:24][CH2:25][O:26][S:27]([CH3:30])(=[O:28])=[O:29])[C:9]1[CH:17]=[C:13]([C:14]([NH:31][CH2:32][CH2:33][OH:34])=[O:16])[C:12]([N+:18]([O-:20])=[O:19])=[CH:11][C:10]=1[N+:21]([O-:23])=[O:22])(=[O:3])=[O:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 700EthanolamineHCID 16115119HCID 16115119, compound

Product 1

HCID 16115123HCID 16115123, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 8 (3.20 g, 6.79 mmol) in SOCl2 (60 mL) containing DMF (2 drops) was heated under reflux for 1 h. Evaporation of the solvent under reduced pressure, followed by azeotroping in with benzene gave the crude acid chloride, which was dissolved in dry Me2CO (80 mL) and treated at 0° C. with 2-aminoethanol (1.24 g, 20.3 mmol). After stirring at 0° C. for 5 min, the mixture was acidified to pH 2-3 with 0.2 N HCl, concentrated to half volume, and then solid NaBr was added. The mixture was extracted with EtOAc (2×) and the combined extracts were washed with saturated NaBr solution, dried (Na2SO4) and evaporated. The residue was chromatographed on silica gel, eluting with EtOAc/MeOH (15:1) to give 2-(5-{[(2-hydroxyethyl)amino]carbonyl} {2-[(methylsulfonyl)oxy]ethyl}-2,4-dinitroanilino)ethyl methanesulfonate (9a) (2.87 g, 82%) as a gum that was used directly.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 h
  3. customEvaporation of the solvent under reduced pressure
  4. customby azeotroping in with benzene
  5. customgave the crude acid chloride, which
  6. dissolutionwas dissolved in dry Me2CO (80 mL)
  7. concentrationconcentrated to half volume
  8. additionsolid NaBr was added
  9. extractionThe mixture was extracted with EtOAc (2×)
  10. washthe combined extracts were washed with saturated NaBr solution
  11. dry with materialdried (Na2SO4)
  12. customevaporated
  13. customThe residue was chromatographed on silica gel
  14. washeluting with EtOAc/MeOH (15:1)

Sources & evidence

ORD record
ord-c81f37b4aa2f490b8fe76ad4429e3412
Source dataset
uspto-grants-2010_08
Patent number
US07776924B2

Reaction notes

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