Sodium Hydroxide → 3-(1,1-Dimethylprop-2-ynylamino)propionaldehyde

HRID 435543Notes

Reaction equation

HRID 435543 reaction equation
[CH3:1][C:2]([NH2:6])([CH3:5])[C:3]#[CH:4].Br[CH2:8][CH2:9][CH:10]=[O:11].[OH-].[Na+]>CO>[CH3:1][C:2]([NH:6][CH2:8][CH2:9][CH:10]=[O:11])([CH3:5])[C:3]#[CH:4]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 763193-Butyn-2-amine, 2-methyl-HCID 124655253-Bromopropanal

Product 1

HCID 214000713-(1,1-Dimethylprop-2-ynylamino)propionaldehyde

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1,1-Dimethylprop-2-ynylamine (1.0 mole), the diethyl acetal of 3-bromopropionaldehyde (1.0 mole) and methanol (100 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture is heated at reflux with stirring for a period of about 6 hours. After this time the reaction mixture is cooled to room temperature and sodium hydroxide (20 grams) is added. The reaction mixture is then stirred for an additional period of about 16 hours. The mixture is then filtered and the filtrate is distilled to yield the desired product the diethyl acetal of 3-(1,1-dimethylprop- 2-ynylamino)propionaldehyde.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. temperatureThe reaction mixture is heated
  4. temperatureat reflux
  5. stirringThe reaction mixture is then stirred for an additional period of about 16 hours
  6. filtrationThe mixture is then filtered
  7. distillationthe filtrate is distilled

Sources & evidence

ORD record
ord-a2cb8a2021234a38922dd2d600e849fc
Source dataset
uspto-grants-1977_02
Patent number
US04006009

Reaction notes

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