Sodium Hydroxide → HCID 21955123, compound

HRID 2213048Notes

Reaction equation

HRID 2213048 reaction equation
C1(O)OC2O[CH:8]([OH:12])[CH:9](O)OC2OC1O.[C:15]1([CH2:21][NH:22][CH2:23][CH2:24][NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH-].[Na+]>Cl>[C:15]1([CH2:21][N:22]2[CH2:23][CH2:24][N:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)[C:8](=[O:12])[CH2:9]2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 92988Glyoxal trimeric dihydrate2×HCID 21955371N1-(Phenylmethyl)-N2-2-pyridinyl-1,2-ethanediamine

Product 1

HCID 21955123HCID 21955123, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Glyoxal trimeric dihydrate (15.8 g, 75 mmol) was added to a mixture of N-phenylmethyl-N′-(2-pyridinyl)-1,2-ethanediamine (Description 146, 5.7 g, 25 mmol) and hydrochloric acid (2N, 100 mL) and the mixture was stirred at room temperature for 24 hours. Further glyoxal trimeric dihydrate (5.3 g, 25 mmol) was added and the mixture was stirred at room temperature for 20 hours. The mixture was basified with aqueous sodium hydroxide (4M) and extracted with ethyl acetate (2×200 mL). The combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with isohexane/EtOAc (40:60 increasing to 30:70), to give the title compound as a light brown oil (3.6 g, 54%). m/z (ES+) 268 (M+1).

Workup

  1. stirringthe mixture was stirred at room temperature for 20 hours
  2. extractionextracted with ethyl acetate (2×200 mL)
  3. dry with materialThe combined organic fractions were dried (MgSO4)
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by flash column chromatography on silica gel eluting with isohexane/EtOAc (40:60 increasing to 30:70)

Sources & evidence

ORD record
ord-5bc23f5bf96049b69623f47d38f7459a
Source dataset
uspto-grants-2006_09
Patent number
US07105507B2

Reaction notes

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