Bromoacetyl bromide → 2-(Bromoacetyl)amino-N-(5-chloropyridin-2-yl)benzamide

HRID 1247043

Reaktionsgleichung

Reaktionsgleichung von HRID 1247043
[NH2:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][N:8]=1)=[O:5].[Br:18][CH2:19][C:20](Br)=[O:21]>O1CCCC1.C(N(C(C)C)CC)(C)C.C(OCC)(=O)C.O>[Br:18][CH2:19][C:20]([NH:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][N:8]=1)=[O:5])=[O:21]

Komponenten

7

Edukt 2

HCID 61147Bromoacetyl bromideHCID 219063812-amino-N-(5-chloropyridin-2-yl)benzamide

Produkt 1

HCID 219063592-(Bromoacetyl)amino-N-(5-chloropyridin-2-yl)benzamideAusbeute 89,6 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 81531DiisopropylethylamineLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-amino-N-(5-chloropyridin-2-yl)benzamide (1.65 g, 6.66 mmol) in tetrahydrofuran (60 mL) and diisopropylethyl amine (1.28 mL) was added bromoacetyl bromide (0.64 mL, 7.32 mmol) dropwise at 0° C. The reaction mixture was warmed to room temperature and stirred overnight. Diluted the reaction mixture with ethyl acetate (120 mL) and water (50 mL). Separated the organic layer and washed with water (25 mL), saturated sodium bicarbonate (50 mL), 0.2 N hydrochloric acid (25 mL), water (50 mL). Dried over sodium sulfate and remove the solvent to get crude product (2.2 g), which was used as such in the following step.

Aufarbeitung

  1. customSeparated the organic layer
  2. washwashed with water (25 mL), saturated sodium bicarbonate (50 mL), 0.2 N hydrochloric acid (25 mL), water (50 mL)
  3. dry with materialDried over sodium sulfate
  4. customremove the solvent

Quellen und Nachweise

ORD-Eintrag
ord-053255370c4843838465b713191e6951
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129245B2

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