Acetic Anhydride → HCID 20394564, compound

HRID 261621Notes

Reaction equation

HRID 261621 reaction equation
[C:1]([NH:9][CH2:10][CH2:11][CH2:12][C:13]1[C:17](=[O:18])[O:16][CH:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25](OC(=O)C)(=O)C.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(O)(=O)C>[C:15]([NH:14][CH:13]([CH2:12][CH2:11][CH2:10][NH:9][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:17](=[O:18])[CH3:25])(=[O:16])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 70607641HCID 70607641, compound

Product 1

HCID 20394564HCID 20394564, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 4-(3-benzamidopropyl)-2-phenyl-5-oxazolone (1.0 g, 3.1 m.mol), 4-dimethylaminopyridine (0.016 g), acetic anhydride (0.62 ml) and triethylamine (0.62 ml) was stirred for one hour. Acetic acid (4.7 ml) was added and the solution was set aside overnight and evaporated to dryness. The residue was dissolved in chloroform and washed with dilute NaOH, dilute HCl and then dried over MgSO4. Concentration gave the crude product which could be purified by dry-column chromatography on alumina with ethyl acetate as solvent to give 3,6-dibenzamidohexan-2-one.

Workup

  1. waitthe solution was set aside overnight
  2. customevaporated to dryness
  3. dissolutionThe residue was dissolved in chloroform
  4. washwashed with dilute NaOH, dilute HCl
  5. dry with materialdried over MgSO4
  6. concentrationConcentration
  7. customgave the crude product which
  8. customcould be purified by dry-column chromatography on alumina with ethyl acetate as solvent

Sources & evidence

ORD record
ord-433a1403d0ef4918b0a3558e7b900363
Source dataset
uspto-grants-1979_08
Patent number
US04166184

Reaction notes

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