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

HRID 1247043

Reaction equation

HRID 1247043 reaction equation
[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]

Participants

7

Reactant 2

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

Product 1

HCID 219063592-(Bromoacetyl)amino-N-(5-chloropyridin-2-yl)benzamideYield 89.6%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 81531DiisopropylethylamineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-053255370c4843838465b713191e6951
Source dataset
uspto-grants-2006_10
Patent number
US07129245B2

Linked notes

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