Acetic Anhydride → HCID 13371391, compound

HRID 2412810Notes

Reaction equation

HRID 2412810 reaction equation
[C:1]([N:9]([CH2:11][C:12](O)=O)[CH3:10])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(=O)C)(=O)C.[C:22]1(=[O:33])[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25](=[O:32])[CH:24]=C1>C1(C)C=CC=CC=1>[CH3:10][N:9]1[C:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:24]2[C:12]([C:22](=[O:33])[C:31]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:25]2=[O:32])=[CH:11]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 85301,4-NaphthoquinoneHCID 75728Glycine, N-benzoyl-N-methyl-

Product 1

HCID 13371391HCID 13371391, compoundYield 19.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-Benzoylsarcosine (3.86 g, 0.020 mol) was dissolved in 7 mL (0.070 mol) of acetic anhydride and heated until a yellow color was observed. Forty milliliters of toluene was added to the reaction flask after the color change was observed. After stirring for 15 minutes, 3.16 g (0.020 mol) of 1,4-naphthoquinone was added. The resulting black mixture was heated for 1.5 hours, then stirred at room temperature overnight. The mixture was filtered to yield 1.13 g (19%) of yellow-brown solid. The solid was recrystallized several times from toluene to give bright yellow crystals: mp 268°-271° C.; IR 1655 and 1645 (C=0) cm-1 ; H-1 NMR (CDCl3) δ 3.60 (s, 3, NCH3), 7.10-7.75 (complex m and s, 8, ArH and pyrrole H), 7.95-8.30 (m, 2, ArH); MS m/e 287 M+.

Workup

  1. temperatureheated until a yellow color
  2. temperatureThe resulting black mixture was heated for 1.5 hours
  3. stirringstirred at room temperature overnight
  4. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-f03c775429f643218ddeabb64077a4ee
Source dataset
uspto-grants-1985_01
Patent number
US04494547

Reaction notes

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