Sodium Carbonate → N-(4,5-dimethyl-1,3-dioxolan-2-ylmethyl)-2-propoxyaniline

HRID 28043Notes

Reaction equation

HRID 28043 reaction equation
[CH2:1]([O:4][C:5]1[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=1[NH2:7])[CH2:2][CH3:3].C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:19][CH:20]1[O:24][CH:23]([CH3:25])[CH:22]([CH3:26])[O:21]1>>[CH3:26][CH:22]1[CH:23]([CH3:25])[O:24][CH:20]([CH2:19][NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[O:4][CH2:1][CH2:2][CH3:3])[O:21]1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 21134322-PropoxyanilineHCID 128944572-Bromomethyl-4,5-dimethyl-1,3-dioxolane

Product 1

HCID 23338379N-(4,5-dimethyl-1,3-dioxolan-2-ylmethyl)-2-propoxyaniline

Procedure

2-Propoxyaniline (0.5 mole) and sodium carbonate (30 grams) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. 2-Bromomethyl-4,5-dimethyl-1,3-dioxolane (0.55 mole) is slowly added and the reaction mixture is heated at reflux for a period of about 1 hour. After this time the reaction mixture is filtered and additional sodium carbonate (5 grams) is added to the filtrate. The mixture is then distilled under reduced pressure to yield the desired product N-(4,5-dimethyl-1,3-dioxolan-2-ylmethyl)-2-propoxyaniline.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. temperaturethe reaction mixture is heated
  4. temperatureat reflux for a period of about 1 hour
  5. filtrationAfter this time the reaction mixture is filtered
  6. additionadditional sodium carbonate (5 grams) is added to the filtrate
  7. distillationThe mixture is then distilled under reduced pressure

Sources & evidence

ORD record
ord-9cc5f3ae89ae4e3899260a2c342215b3
Source dataset
uspto-grants-1980_09
Patent number
US04225335

Reaction notes

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