Hydrochloric Acid → HCID 58396412, Verbindung

HRID 446267

Reaktionsgleichung

Reaktionsgleichung von HRID 446267
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=O.[CH2:12]1[N:17]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][C:19]=2[NH2:28])[CH2:16][CH2:15][O:14][CH2:13]1.P(Cl)(Cl)Cl.Cl>CN(C1C=CN=CC=1)C.C1(C)C=CC=CC=1.[Cl-].[Na+].O.C(OCC)(=O)C>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([NH:28][C:19]1[CH:20]=[C:21]([C:24]([F:25])([F:26])[F:27])[CH:22]=[CH:23][C:18]=1[N:17]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)=[O:7]

Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 24387Phosphorus trichlorideHCID 685123-Hydroxy-4-methylbenzoic acidHCID 136624N-(2-Amino-4-(trifluoromethyl)phenyl)morpholine

Produkt 1

HCID 58396412HCID 58396412, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

3-Hydroxy-4-methylbenzoic acid (530 mg, 3.5 mmol), 3-amino-4-(4-morpholino)benzotrifluoride (890 mg, 3.6 mmol), and DMAP (150 mg, 1.3 mmol) were suspended in 20 mL dry toluene in a 2-neck flask with an attached Dean-Stark trap under N2. The mixture was stirred in a 130° C. oil bath and brought to a boil before PCl3 (0.18 mL, 2 mmol) was added dropwise by glass/Teflon syringe over 15 minutes. Heating was continued an additional 45 minutes. After cooling, the mixture was diluted with brine and ethyl acetate, and acidified with 1 N HCl. After extraction, the organic layer was dried with Na2SO4, concentrated, and purified by flash chromatography (2% MeOH in CH2Cl2). The isolated material was packed into a small filtration apparatus and rinsed with a small amount of CH2Cl2 to provide the title compound as a white solid. 1H NMR (Varian, 400 MHz, DMSO-d6) d: 9.83 (s, 1H), 9.50 (s, 1H), 8.45 (s, 1H), 7.48 (m, 1H), 7.43 (m, 1H), 7.34 (s, 1H), 7.31 (m, 1H), 7.25 (m, 1H), 3.78 (m, 4H), 2.90 (m, 4H), 2.18 (s, 3H).

Aufarbeitung

  1. temperatureHeating
  2. temperatureAfter cooling
  3. extractionAfter extraction
  4. dry with materialthe organic layer was dried with Na2SO4
  5. concentrationconcentrated
  6. custompurified by flash chromatography (2% MeOH in CH2Cl2)
  7. washrinsed with a small amount of CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-249d05d5ddf14b259dd33d918ce7fb4b
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476434B2

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