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

HRID 268057Notes

Reaction equation

HRID 268057 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-6909cfbf6a88435b834f782fa39c9540
Source dataset
uspto-grants-1976_03
Patent number
US03946045

Reaction notes

Loading…