5-Chloro-2-methylaniline → N-(1,3-Dioxolan-2-ylmethyl)-2-methyl-5-chloroaniline

HRID 1605042Notes

Reaction equation

HRID 1605042 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:3]=1[NH2:4].Cl[CH2:11][CH:12]1[O:16][CH2:15][CH2:14][O:13]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:13]1[CH2:14][CH2:15][O:16][CH:12]1[CH2:11][NH:4][C:3]1[CH:5]=[C:6]([Cl:9])[CH:7]=[CH:8][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 72605-Chloro-2-methylanilineHCID 11430Potassium CarbonateHCID 757272-(Chloromethyl)-1,3-dioxolane

Product 1

HCID 21548992N-(1,3-Dioxolan-2-ylmethyl)-2-methyl-5-chloroaniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Methyl-5-chloroaniline (75 grams), 2-chloromethyl- 1,3-dioxolane (25 grams), potassium carbonate (22 grams) and dimethylformamide (50 ml) were charged with a glass reaction vessel equipped with a mechanical stirrer, thermometer, and reflux condenser. The reaction mixture was heated, with stirring, for a period of about 26 hours. After this time the reaction mixture was filtered and then distilled to yield the desired product N-(1,3-dioxolan-2-ylmethyl)-2-methyl-5-chloroaniline having a boiling point of 116° to 118°C at 0.1 mm of Hg pressure.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer, and reflux condenser
  3. temperatureThe reaction mixture was heated
  4. filtrationAfter this time the reaction mixture was filtered
  5. distillationdistilled

Sources & evidence

ORD record
ord-6019f93dcf044c32878d5347ef049ef3
Source dataset
uspto-grants-1976_04
Patent number
US03948950

Reaction notes

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