Benzene → 2,2,5-Trimethyl-3(2',3'-dibromopropionyl)oxazolidine

HRID 2287023Notes

Reaction equation

HRID 2287023 reaction equation
C1C=CC=CC=1.[CH3:7][C:8]1([CH3:14])[NH:12][CH2:11][CH:10]([CH3:13])[O:9]1.C(N(CC)CC)C.[Br:22][CH:23]([CH2:27][Br:28])[C:24](Cl)=[O:25]>O>[CH3:7][C:8]1([CH3:14])[N:12]([C:24](=[O:25])[CH:23]([Br:22])[CH2:27][Br:28])[CH2:11][CH:10]([CH3:13])[O:9]1

Participants

6

Reactant 4

HCID 241Benzene2×HCID 8471TriethylamineHCID 867902,3-Dibromopropanoyl chlorideHCID 95486Oxazolidine, 2,2,5-trimethyl-

Product 1

HCID 129068282,2,5-Trimethyl-3(2',3'-dibromopropionyl)oxazolidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Fourteen (14 ml.) milliliters of a benzene solution containing 3.5 g. of 2,2,5-trimethyl oxazolidine was added to 25 ml. of benzene and 3.5 g. of triethylamine. Seven and one-half (7.5 g.) grams of 2,3-dibromopropionyl chloride was added dropwise with stirring and cooling in an ice bath. When reaction was complete, the mixture was poured into water and the benzene layer separated, dried over anhydrous magnesium sulfate and the solvent stripped under vacuum. The yield was 5.7 g. of an oil, nD30 =1.5060.

Workup

  1. temperaturecooling in an ice bath
  2. customWhen reaction
  3. customthe benzene layer separated
  4. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-80984e82e37d43819810b1c1b852cab9
Source dataset
uspto-grants-1981_05
Patent number
US04268677

Reaction notes

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