Chloroacetyl chloride → 2-chloro-N-(thiazol-4-yl)methyl-N-(2-ethyl-6-methylphenyl)acetamide

HRID 1156485Notes

Reaction equation

HRID 1156485 reaction equation
[S:1]1[CH:5]=[C:4]([CH2:6][NH:7][C:8]2[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:15][CH3:16])[N:3]=[CH:2]1.[Cl:17][CH2:18][C:19](Cl)=[O:20]>C1(C)C=CC=CC=1>[Cl:17][CH2:18][C:19]([N:7]([CH2:6][C:4]1[N:3]=[CH:2][S:1][CH:5]=1)[C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:15][CH3:16])=[O:20]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 20534534N-(thiazol-4-yl)methyl-2-ethyl-6-methylaniline

Product 1

HCID 130376002-chloro-N-(thiazol-4-yl)methyl-N-(2-ethyl-6-methylphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3.5 g N-(thiazol-4-yl)methyl-2-ethyl-6-methylaniline (from Example 11) and 125 ml toluene was heated to reflux and 1.7 g chloroacetyl chloride was added dropwise. The mixture was refluxed for 2 hours, cooled, stripped and purified on a silica-gel column using methylene chloride followed by 2% methanol:methylene chloride. C15H17ClN2O5 : calc., %C 58.35,%H 5.51, %N, 9.08; found, %C 57.07, %H 5.58, %N 7.81.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureThe mixture was refluxed for 2 hours
  4. temperaturecooled
  5. custompurified on a silica-gel column

Sources & evidence

ORD record
ord-8189df78d1dd4939ae8800a3db032ca8
Source dataset
uspto-grants-1982_06
Patent number
US04336059

Reaction notes

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