Benzene → N-(2-methyl-1,3-dioxolan-5-ylmethyl)-2-t-butyl-alpha-bromoacetanilide

HRID 596751Notes

Reaction equation

HRID 596751 reaction equation
[CH3:1][CH:2]1[O:6][CH2:5][CH:4]([CH2:7][NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2C(C)(C)C)[O:3]1.[C:19](=O)([O-])[O-].[Na+].[Na+].O.[Br:26][CH2:27][C:28](Cl)=[O:29].[CH:31]1[CH:36]=[CH:35]C=CC=1>>[CH3:1][CH:2]1[O:6][CH2:5][CH:4]([CH2:7][N:8]([C:28](=[O:29])[CH:27]([C:36]([CH3:35])([CH3:31])[CH3:19])[Br:26])[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[O:3]1

Participants

6

Reactant 5

HCID 241BenzeneHCID 962WaterHCID 10340Sodium CarbonateHCID 89602Bromoacetyl chlorideHCID 21447793N-(2-Methyl-1,3-dioxolan-5-ylmethyl)-2-t-butylaniline

Product 1

HCID 21447810N-(2-methyl-1,3-dioxolan-5-ylmethyl)-2-t-butyl-alpha-bromoacetanilide

Procedure

N-(2-Methyl-1,3-dioxolan-5-ylmethyl)-2-t-butylaniline (0.1 mole), sodium carbonate (0.1 mole), water (10 ml) and benzene (100 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The reaction mixture is cooled to a temperature of about 0° C and bromoacetyl chloride (0.11 mole) is incrementally added with stirring. After the addition is completed, stirring is continued for a period of about one hour. The mixture is then washed with water, dried over anhydrous magnesium sulfate and filtered. The filtrate is stripped of solvent and unreacted starting materials to yield the desired product N-(2-methyl-1,3-dioxolan-5-ylmethyl)-2-t-butyl-α-bromoacetanilide as the residue.

Workup

  1. customequipped with a mechanical stirrer
  2. additionis incrementally added
  3. additionAfter the addition
  4. stirringstirring
  5. washThe mixture is then washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered

Sources & evidence

ORD record
ord-9f453d3a7ece42ea8d666db1b7307af8
Source dataset
uspto-grants-1977_03
Patent number
US04012222

Reaction notes

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