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Benzene → N-(1,1-dimethylprop-2-ynyl)-N-(4,5-dimethyl-1,3-dioxolan-2-ylmethyl)-alpha-bromopropionamide

HRID 1763787
Notes
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Reaction equation

HRID 1763787 reaction equation
[CH3:1][C:2]([NH:6][CH2:7][CH:8]1[O:12][CH:11]([CH3:13])[CH:10]([CH3:14])[O:9]1)([CH3:5])[C:3]#[CH:4].C1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].[Br:27][CH:28]([CH3:32])[C:29](Cl)=[O:30]>O>[CH3:5][C:2]([N:6]([CH2:7][CH:8]1[O:9][CH:10]([CH3:14])[CH:11]([CH3:13])[O:12]1)[C:29](=[O:30])[CH:28]([Br:27])[CH3:32])([CH3:1])[C:3]#[CH:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 241BenzeneHCID 10340Sodium CarbonateHCID 979802-Bromopropanoyl chlorideHCID 20307430HCID 20307430, compound

Product 1

HCID 20307433N-(1,1-dimethylprop-2-ynyl)-N-(4,5-dimethyl-1,3-dioxolan-2-ylmethyl)-alpha-bromopropionamide

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

N-(1,1-Dimethylprop-2-ynyl)-N-(4,5-dimethyl-1,3-dioxolan-2-ylmethyl)amine (10 grams), benzene (100 ml), water (100 ml) and sodium carbonate (8 grams) are charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The reaction mixture is cooled to a temperature of 5° to 10° C. and α-bromopropionyl chloride (7 grams) is added dropwise with stirring. After the addition is completed stirring is continued until the reaction mixture reaches room temperature. After this time the organic phase is separated from the aqueous phase and is washed with water. The washed solution is then dried over anhydrous magnesium sulfate, filtered and stripped of solvent under reduced pressure to yield the desired product N-(1,1-dimethylprop-2-ynyl)-N-(4,5-dimethyl-1,3-dioxolan-2-ylmethyl)-α-bromopropionamide.

Workup

  1. customequipped with a mechanical stirrer
  2. additionis added dropwise
  3. additionAfter the addition
  4. stirringis completed stirring
  5. customreaches room temperature
  6. customAfter this time the organic phase is separated from the aqueous phase
  7. washis washed with water
  8. dry with materialThe washed solution is then dried over anhydrous magnesium sulfate
  9. filtrationfiltered

Sources & evidence

ORD record
ord-8fd29abf78944d6b87ed31d10ffd5cbf
Source dataset
uspto-grants-1978_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04113464

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes