Acetic Anhydride → HCID 57397373, Verbindung

HRID 2076035Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2076035
[C:1](OC(=O)C)(=O)[CH3:2].[CH3:8][O:9][C:10]1[CH:19]=[C:18]([NH:20][C:21]2[S:22][C:23]3[CH2:29][CH2:28][CH2:27][CH:26]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:24]=3[N:25]=2)[CH:17]=[CH:16][C:11]=1[C:12]([NH:14][NH2:15])=[O:13]>CN(C)C=O>[CH3:8][O:9][C:10]1[CH:19]=[C:18]([NH:20][C:21]2[S:22][C:23]3[CH2:29][CH2:28][CH2:27][CH:26]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:24]=3[N:25]=2)[CH:17]=[CH:16][C:11]=1[C:12]1[O:13][C:1]([CH3:2])=[N:15][N:14]=1

Komponenten

4

Edukt 2

HCID 7918Acetic AnhydrideHCID 86632604HCID 86632604, Verbindung

Produkt 1

HCID 57397373HCID 57397373, VerbindungAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

At room temperature, acetic anhydride (108 μL) was added to a suspension of 2-methoxy-4-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-ylamino)-benzoic acid hydrazide (130 mg, 0.33 mmol) in dimethylformamide (5 mL). The mixture was stirred for 40 hours and evaporated to dryness. The residue was taken up in 10% w/w (3 mL) phosphorous pentoxide in methanesulfonic acid (prepared by mixing 5 g phosphorous pentoxide and 30 mL methanesulfonic acid and stirring for 2 h at 90° C.) and stirred for 18 hours. The mixture was poured into 75 ml water, neutralized to pH 5-6 with 32% aqueous sodium hydroxide and the precipitate filtered off. The solid was dissolved in ethyl acetate (30 mL), washed four times with water and once with brine, dried with magnesium sulfate and concentrated in vacuo, affording the title compound (69 mg, 65%) as an off-white solid. NMR (CDCl3, 300 MHz): δ (ppm)=7.74 (d, 1H), 7.61 (d, 1H), 7.31-7.15 (m, 5H), 6.82 (dd, 1H), 4.03 (m, 1H), 3.34 (m, 3H), 2.73 (m, 2H), 2.50 (m, 3H), 2.14 (m, 1H), 1.79 (m, 3H). MS ISP (m/e): 419.1 (100) (M+H)+.

Aufarbeitung

  1. customevaporated to dryness
  2. customwas taken up in 10% w/w (3 mL) phosphorous pentoxide in methanesulfonic acid (prepared by mixing 5 g phosphorous pentoxide and 30 mL methanesulfonic acid and stirring for 2 h at 90° C.)
  3. stirringstirred for 18 hours
  4. additionThe mixture was poured into 75 ml water
  5. filtrationthe precipitate filtered off
  6. dissolutionThe solid was dissolved in ethyl acetate (30 mL)
  7. washwashed four times with water
  8. dry with materialonce with brine, dried with magnesium sulfate
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b3cba06d47aa436bb2cbc7508feb50ed
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07923450B2

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