Water → HCID 15345698, compound

HRID 259786Notes

Reaction equation

HRID 259786 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:10][CH2:11][N:12]([C:16]1[CH:17]=[C:18]([CH:23]=[CH:24][CH:25]=1)[C:19]([O:21][CH3:22])=[O:20])[CH2:13][CH2:14]Cl.O>CC(C)=O>[CH2:1]([N:8]1[CH2:10][CH2:11][N:12]([C:16]2[CH:17]=[C:18]([CH:23]=[CH:24][CH:25]=2)[C:19]([O:21][CH3:22])=[O:20])[CH2:13][CH2:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7504BenzylamineHCID 32688Benzoic acid, m-(bis(2-chloroethyl)amino)-, methyl ester

Product 1

HCID 15345698HCID 15345698, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Benzylamine (1.2 mL, 11 mmol), 120b (1.0 g, 3.6 mmol), water (50 mL), and acetone (50 mL) were heated at reflux for 28 h, then stirred at room temperature an additional 41 h. After evaporation of the acetone, the mixture was extracted with EtOAc (2×). The organic phase was extracted further with water and brine, then dried (Na2SO4), filtered and concentrated. The product was purified by chromatography on silica gel, eluting with 30% to 50% EtOAc in hexanes, then evaporated to yield a yellow oil (0.57 g). IR(neat): cm-1 1722. 1H NMR (300 MHz, CDCl3): 7.57-7.08 (m, 9H), 3.88 (s, 3H), 3.56 (s, 2H), 3.24 (m, 4H), 2.61 (m, 4H). HR-MS: Calc'd. 311.1760, Found 311.1764.

Workup

  1. temperatureat reflux for 28 h
  2. customAfter evaporation of the acetone
  3. extractionthe mixture was extracted with EtOAc (2×)
  4. extractionThe organic phase was extracted further with water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was purified by chromatography on silica gel
  9. washeluting with 30% to 50% EtOAc in hexanes
  10. customevaporated

Sources & evidence

ORD record
ord-37eb8c67f6554d40acd6487f66fa56be
Source dataset
uspto-grants-1996_06
Patent number
US05523302

Reaction notes

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