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

HRID 28044

Reaction equation

HRID 28044 reaction equation
[CH2:1]([O:5][C:6]1[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=1[NH2:8])[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:20][CH:21]1[O:25][CH:24]([CH3:26])[CH:23]([CH3:27])[O:22]1>>[CH3:27][CH:23]1[CH:24]([CH3:26])[O:25][CH:21]([CH2:20][NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][CH2:1][CH2:2][CH2:3][CH3:4])[O:22]1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 1382652-ButoxyanilineHCID 128944572-Bromomethyl-4,5-dimethyl-1,3-dioxolane

Product 1

HCID 23338378N-(4,5-dimethyl-1,3-dioxolan-2-ylmethyl)-2-n-butoxyaniline

Conditions

Temperature
100 °C

Procedure

2-n-Butoxyaniline (99 grams; 0.6 moles) and sodium carbonate (31.6 grams) were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. 2-Bromomethyl-4,5-dimethyl-1,3-dioxolane (25 ml) was added and the reaction mixture was heated at a temperature of about 100° C. for a period of about 4 hours. After this time the reaction mixture was filtered and additional sodium carbonate (5.0 grams) was added to the filtrate. The mixture was then vacuum distilled and the fraction boiling at 123° C. and 0.05 mm of Hg pressure was collected to yield the desired product N-(4,5-dimethyl-1,3-dioxolan-2-ylmethyl)-2-n-butoxyaniline.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. filtrationAfter this time the reaction mixture was filtered
  4. additionadditional sodium carbonate (5.0 grams) was added to the filtrate
  5. distillationvacuum distilled
  6. customthe fraction boiling at 123° C. and 0.05 mm of Hg pressure was collected

Sources & evidence

ORD record
ord-0eabac01f602400795b8517efba6e5fe
Source dataset
uspto-grants-1980_09
Patent number
US04225335

Linked notes

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