Water → N-methyl-benzimidic acid 1,3-dioxo-1,3-dihydro-isoindol-2-yl ester

HRID 2240918

Reaktionsgleichung

Reaktionsgleichung von HRID 2240918
[Na].[OH:2][N:3]1[C:7](=[O:8])[C:6]2=[CH:9][CH:10]=[CH:11][CH:12]=[C:5]2[C:4]1=[O:13].[CH3:14][N:15]=[C:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CN(C=O)C>[O:8]=[C:7]1[C:6]2[C:5](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4](=[O:13])[N:3]1[O:2][C:16](=[N:15][CH3:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 576277N-Methylbenzimidoyl chlorideHCID 6754951570206-52-9

Produkt 1

HCID 59305847N-methyl-benzimidic acid 1,3-dioxo-1,3-dihydro-isoindol-2-yl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

N-hydroxy phthalimide sodium salt (46.25 g.; 0.25 mol), is dissolved in dry DMF (220 ml), to the resulting suspension 38.8 g (0.25 mol) of N-methyl benzimidoyl chloride (prepared according to J. C. S. Perkin II, 1324, (1980)) are slowly added at room temperature, on stirring. The reaction mixture is stirred at room temperature for 19 h and then poured into 1.5 l of water. The so formed precipitate is sucked off and dried in vacuo to obtain 66.06 g of a a crude product which is then taken up in 250 ml of acetonitrile. After filtration 58.7 g of N-methyl-benzimidic acid 1,3-dioxo-1,3-dihydro-isoindol-2-yl ester are obtained in form of colorless crystals, mp. 174-176° C.

Aufarbeitung

  1. additionare slowly added at room temperature
  2. stirringThe reaction mixture is stirred at room temperature for 19 h
  3. customThe so formed precipitate
  4. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5f0a33363701454c8f911a2ac82d2d4a
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723399B2

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