Chloroacetyl chloride → 2-chloro-N-(2-ethoxyethyl)-N-(3-nitro-2-pyridinyl)acetamide

HRID 1533951Notes

Reaction equation

HRID 1533951 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][NH:6][C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[CH:9][N:8]=1)[CH3:2].[Cl:16][CH2:17][C:18](Cl)=[O:19]>O1CCOCC1>[Cl:16][CH2:17][C:18]([N:6]([CH2:5][CH2:4][O:3][CH2:1][CH3:2])[C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[CH:9][N:8]=1)=[O:19]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 15718757N-(2-Ethoxyethyl)-3-nitropyridin-2-amine

Product 1

HCID 199115422-chloro-N-(2-ethoxyethyl)-N-(3-nitro-2-pyridinyl)acetamideYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 42.24 parts of N-(2-ethoxyethyl)-3-nitro-2-pyridinamine in 309 parts of 1,4-dioxane were added 49.7 parts of 2-chloroacetyl chloride. The reaction mixture was stirred for 4 hours at reflux temperature. The whole was evaporated and the residue was taken up in methylbenzene. The organic layer was evaporated again, yielding 57.5 parts (100%) of 2-chloro-N-(2-ethoxyethyl)-N-(3-nitro-2-pyridinyl)acetamide as a residue (int. 1).

Workup

  1. temperatureat reflux temperature
  2. customThe whole was evaporated
  3. customThe organic layer was evaporated again

Sources & evidence

ORD record
ord-9d7e5b8b04be4adaa7c76e268ba1ea0d
Source dataset
uspto-grants-1992_02
Patent number
US05086056

Reaction notes

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