Dichloromethane → 5-Chloro-2-(2-methyl-acryloylamino)-benzamide

HRID 555257

Reaction equation

HRID 555257 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].C[CH:13]=[CH:14][C:15](Cl)=[O:16].[CH2:18](Cl)Cl>>[Cl:11][C:8]1[CH:9]=[CH:10][C:2]([NH:1][C:15](=[O:16])[C:14]([CH3:18])=[CH2:13])=[C:3]([CH:7]=1)[C:4]([NH2:6])=[O:5]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 788762-Amino-5-chlorobenzamideHCID 790802-Butenoyl chloride

Product 1

HCID 589496945-Chloro-2-(2-methyl-acryloylamino)-benzamide

Procedure

2-Amino-5-chloro-benzamide (2.5 mmoL), a literature known compound, was treated with TEA (3.0 mmoL) followed by methylacryl chloride (2.5 mmoL) in DCM at 0° C. The reaction was slowly warmed to room temperature and kept for another 2 h. The reaction mixture was then partitioned between DCM and water. The organic layer was washed with sat. Na2CO3, brine, dried over anhydrous Na2SO4, filtered, concentrated and purified by silica gel column chromatography to afford the title compound as a white solid.

Workup

  1. additionwas treated with TEA (3.0 mmoL)
  2. customThe reaction mixture was then partitioned between DCM and water
  3. washThe organic layer was washed with sat. Na2CO3, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-9b239ee410874131801acfbc5a613f8b
Source dataset
uspto-grants-2011_11
Patent number
US08053441B2

Linked notes

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