Water → 1-(Tert-butyldiphenylsilyloxymethyl)-2,6-dimethyl-3-(phthalimidoacetylamino)benzene

HRID 636492Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 636492
[NH2:1][C:2]1[C:3]([CH3:28])=[C:4]([CH2:9][O:10][Si:11]([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:5]([CH3:8])=[CH:6][CH:7]=1.[C:29]1(=[O:43])[N:33]([CH2:34][C:35](Cl)=[O:36])[C:32](=[O:38])[C:31]2=[CH:39][CH:40]=[CH:41][CH:42]=[C:30]12.O>N1C=CC=CC=1.CN(C)C=O>[Si:11]([O:10][CH2:9][C:4]1[C:5]([CH3:8])=[CH:6][CH:7]=[C:2]([NH:1][C:35](=[O:36])[CH2:34][N:33]2[C:32](=[O:38])[C:31]3=[CH:39][CH:40]=[CH:41][CH:42]=[C:30]3[C:29]2=[O:43])[C:3]=1[CH3:28])([C:24]([CH3:25])([CH3:27])[CH3:26])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 812422H-Isoindole-2-acetyl chloride, 1,3-dihydro-1,3-dioxo-HCID 107391063-Amino-1-(tert-butyldiphenylsilyloxymethyl)-2,6-dimethylbenzene

Produkt 1

HCID 105074021-(Tert-butyldiphenylsilyloxymethyl)-2,6-dimethyl-3-(phthalimidoacetylamino)benzeneAusbeute 94,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a suspension of 3-amino-1-(tert-butyldiphenylsilyloxymethyl)-2,6-dimethylbenzene (42.4 g) in pyridine (17.2 g) and dimethylformamide (212 ml) was dropwise added phthalimidoacetyl chloride (25.6 g) over the period of 15 minutes under ice-cooling, and the mixture was stirred for 1 hour at the same temperature. To the reaction mixture was added water, and the resulting precipitates were collected by filtration and washed with acetonitrile to give 1-(tert-butyldiphenylsilyloxymethyl)-2,6-dimethyl-3-(phthalimidoacetylamino)benzene (59.1 g) as colorless crystals.

Aufarbeitung

  1. customover the period of 15 minutes
  2. temperaturecooling
  3. customthe resulting precipitates
  4. filtrationwere collected by filtration
  5. washwashed with acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-75f73dd2c7e74aa9bea5384e06a66f71
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06194396B1

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