Acetic Acid → 2-Chloro-2',3',6'-trimethylacetanilide

HRID 1856301Notes

Reaction equation

HRID 1856301 reaction equation
[CH3:1][C:2]1[C:8]([CH3:9])=[CH:7][CH:6]=[C:5]([CH3:10])[C:3]=1[NH2:4].C(O)(=O)C.[Cl:15][CH2:16][C:17](Cl)=[O:18].O.O.O.C([O-])(=O)C.[Na+]>O>[Cl:15][CH2:16][C:17]([NH:4][C:3]1[C:5]([CH3:10])=[CH:6][CH:7]=[C:8]([CH3:9])[C:2]=1[CH3:1])=[O:18]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6577Chloroacetyl chlorideHCID 119589472,3,6-TrimethylanilineHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 125468362-Chloro-2',3',6'-trimethylacetanilide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7.8 g of 2,3,6-trimethylaniline R. A. Scherrer and H. R. Beatty, J. Org. Chem. 37, 1681 (1972), and 50 ml glacial acetic acid was cooled to 10° C. in a glass stoppered bottle, 7.23 g chloroacetyl chloride was added, mixed quickly and followed immediately by a cooled solution of 19.3 g sodium acetate trihydrate in 80 ml water. The mixture was shaked for 30 min. and the solid material was filtered off and washed carefully with water. After drying, a yield of 9.94 g (81%) was obtained. It melted at 145°-146° C. Analysis: Calcd. for C11H14ClNO: C 62.4, H 6.67, Cl 16.8. Found: C 62.4, H 6.78, Cl 16.8.

Workup

  1. additionwas added
  2. additionmixed quickly
  3. filtrationthe solid material was filtered off
  4. washwashed carefully with water
  5. customAfter drying
  6. customa yield of 9.94 g (81%) was obtained

Sources & evidence

ORD record
ord-d72351e1be764624bc9fdabf00a86bdf
Source dataset
uspto-grants-1980_08
Patent number
US04218477

Reaction notes

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