Chloroacetyl chloride → HCID 19911565, compound

HRID 1533952Notes

Reaction equation

HRID 1533952 reaction equation
C(OCC[C:6]1[CH:11]=[CH:10][N:9]=[C:8]([NH2:12])[C:7]=1[NH2:13])C.[Cl:14][CH2:15][C:16](Cl)=[O:17].[O:19]1[CH2:24][CH2:23]O[CH2:21][CH2:20]1>>[Cl:14][CH2:15][C:16]([NH:12][C:8]1[C:7]([NH:13][CH2:21][CH2:20][O:19][CH2:24][CH3:23])=[CH:6][CH:11]=[CH:10][N:9]=1)=[O:17]

Participants

4

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 312751,4-DioxaneHCID 19911480HCID 19911480, compound

Product 1

HCID 19911565HCID 19911565, compoundYield 70.4%

Procedure

To a stirred solution of 3.8 parts of N3 -(2-ethoxyethyl)-2,3-pyridinediamine in 50 parts of 1,4-dioxane were added 5.64 parts of 2-chloroacetyl chloride. The reaction mixture was stirred for 5 hours at reflux temperature. The reaction mixture was evaporated and the residue was dissolved in methylbenzene. The whole was evaporated again, yielding 3.62 parts (70.4%) of 2-chloro-N-[3-[(2-ethoxyethyl)amino]-2-pyridinyl]acetamide as a residue (int. 24).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. dissolutionthe residue was dissolved in methylbenzene
  4. customThe whole was evaporated again

Sources & evidence

ORD record
ord-a0c8aaeb07d94ef1afcabedb8b98de55
Source dataset
uspto-grants-1992_02
Patent number
US05086056

Reaction notes

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