4-Toluenesulfonyl chloride → HCID 20510480, Verbindung

HRID 1758016Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1758016
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[C:8]([Cl:15])[C:9]([Cl:14])=[C:10]([Cl:13])[C:11]([Cl:12])=[C:4]2[C:3]1=[O:16].[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.C(N(CC)CC)C>O1CCCC1.C(Cl)Cl>[S:23]([O:1][N:2]1[C:3](=[O:16])[C:4]2=[C:11]([Cl:12])[C:10]([Cl:13])=[C:9]([Cl:14])[C:8]([Cl:15])=[C:5]2[C:6]1=[O:7])([C:20]1[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=1)(=[O:25])=[O:24]

Komponenten

6

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 2873594,5,6,7-tetrachloro-2-hydroxy-2,3-dihydro-1H-isoindole-1,3-dione

Produkt 1

HCID 20510480HCID 20510480, VerbindungAusbeute 89,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

N-Tosyloxytetrachlorophthalimide was prepared by the following procedure. To a flask equipped with a stirrer and addition funnel were added N-hydroxytetrachlorophthalimide (10.00 g, 0.033 mol), p-toluenesulfonyl chlorde (6.57 g, 0.033 mol) and 100 mL of dried tetrahydrofuran (THF). A solution of triethylamine (4.5 mL, 0.033 mol) in 20 mL of THF was added dropwise while the reaction vessel was cooled to between -20° and -10°. A red color formed after each drop, and quickly disappeared. After stirring for 2 h at room temperature the reaction mixture was diluted with 200 mL of methylene chloride, and the solution was washed twice with water. The organic layer containing much crystallized product was evaporated, leaving 13.5 g of pale yellow N-tosyloxytetrachlorophthalimide: mp 206°-210°. Recrystallization from toluene (50 mL)-heptane (25 mL) gave 10.7 g (71.5%) of pale yellow product: mp 214°-216°; ir (KBr) 1800 (w), 1740 (vs), 1380 (m), 1190 (m), 1180 (m), 1140 (m), 1025 (m), 810 (m), 790 (m), 725 (m), 705 (m), 506 (m); uv (CH3CN) 240 (58,500), 275 (2990), 328 (2790), 339 nm (3020); mass spectrum 452.8782 (calcd for C15H7NO5Cl4S: m+, 452.8805). Anal. Calcd for C15H7NO5Cl4S: C, 39.59; H, 1.55; N, 3.08; O, 17.58; Cl, 31.16; S, 70.4. Found: C, 40.04, 40.16, 39.70, 39.72; H, 1.95, 1.81, 1.52, 1.70; N, 2.99, 2.89; Cl, 31.30.

Aufarbeitung

  1. customN-Tosyloxytetrachlorophthalimide was prepared by the following procedure
  2. customTo a flask equipped with a stirrer and addition funnel
  3. temperaturewas cooled to between -20° and -10°
  4. customA red color formed after each drop
  5. washthe solution was washed twice with water
  6. additionThe organic layer containing much crystallized product
  7. customwas evaporated

Quellen und Nachweise

ORD-Eintrag
ord-0a52d0e5cd6445978fd970ff36e1c098
Quelldatensatz
uspto-grants-1983_02
Patentnummer
US04371605

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