Hydrochloric Acid → HCID 19356272, Verbindung

HRID 377628Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 377628
[H-].[Na+].[NH2:3][C:4]1[C:9]([Cl:10])=[CH:8][N:7]=[C:6](Cl)[CH:5]=1.[CH3:12][O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][C:15]=1[O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[ClH:41]>O1CCCC1>[Cl:41][C:5]1[CH:6]=[N:7][CH:8]=[C:9]([Cl:10])[C:4]=1[NH:3][C:18](=[O:19])[C:17]1[CH:21]=[CH:22][C:14]([O:13][CH3:12])=[C:15]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:16]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 19356271HCID 19356271, VerbindungHCID 222840492,5-Dichloropyridin-4-amine

Produkt 1

HCID 19356272HCID 19356272, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

To a magnetically stirred suspension of 60% sodium hydride (60% in mineral oil) (0.53 grams) in anhydrous tetrahydrofuran (20 ml) at 0° C. is added a solution of 4-amino-2,5-dichloropyridine (0.90 grams) in anhydrous tetrahydrofuran (20 ml). After stirring for 30 minutes at room temperature the reaction mixture is cooled to 0° C. and treated with a solution of 4-methoxy-3-(11-phenylundecyloxy)benzoyl chloride (2.30 grams) in tetrahydrofuran (20 ml). After stirring at room temperature for 16 hours the reaction mixture is poured into 50 ml of 1N hydrochloric acid and extracted with ethyl acetate. The combined organics are washed with 1N hydrochloric acid, water and brine and then dried over sodium sulfate and concentrated under reduced pressure. The resulting yellow solid is purified by column chromatography on a silica gel column using a ratio of 9:1 mixture of methylene chloride and ethyl acetate as eluent to give 1.9 grams of an off-white solid. MP 114-5° C.; MS m/z 543, 545; Anal. calcd for C30H36Cl2N2O3 : C, 66.29; H, 6.68; N, 5.15. Found: C, 6646; H, 6.61; N, 5.08

Aufarbeitung

  1. temperatureis cooled to 0° C.
  2. stirringAfter stirring at room temperature for 16 hours the reaction mixture
  3. extractionextracted with ethyl acetate
  4. washThe combined organics are washed with 1N hydrochloric acid, water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting yellow solid is purified by column chromatography on a silica gel column
  8. additiona ratio of 9:1 mixture of methylene chloride and ethyl acetate as eluent

Quellen und Nachweise

ORD-Eintrag
ord-d4595b85cd48460d82d91e39c7c5f911
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06028086

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