Triethylamine → HCID 21111949, compound

HRID 2167434Notes

Reaction equation

HRID 2167434 reaction equation
[CH2:1]([N:3](CC)CC)[CH3:2].[Cl:8][C:9]1[C:18]([C:19](Cl)=[O:20])=[C:17]([S:22]([CH3:25])(=[O:24])=[O:23])[CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12].Br.NCCBr>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:8][C:9]1[C:18]([C:19]2[O:20][CH2:2][CH2:1][N:3]=2)=[C:17]([S:22]([CH3:25])(=[O:24])=[O:23])[CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27742172-Bromoethylamine hydrobromide2×HCID 18517408Methyl 2-chloro-3-chlorocarbonyl-4-methylsulfonylbenzoate

Product 1

HCID 21111949HCID 21111949, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

At room temperature, 41.8 g (0.41 mol) of triethylamine and then 31.1 g (0.10 mol) of methyl 2-chloro-3-chlorocarbonyl-4-methylsulfonylbenzoate in 150 ml of toluene were added dropwise to 26.6 g (0.13 mol) of 1-amino-2-bromoethane hydrobromide in 5.00 ml of toluene. The mixture was heated under reflux for 5 hours and then stirred at room temperature for 12 hours, another 5.0 g (0.02 mol) of 1-amino-2-bromoethane hydrobromide were added and the mixture was heated under reflux for 7.5 hours. The reaction mixture was allowed to cool, diluted with ethyl acetate, washed with water, dried and concentrated. The residue was then recrystallized from methyl tert-butyl ether/ethyl acetate. 14.5 g (46% of theory) of methyl 2-chloro-4-methylsulfonyl-3-(4,5-dihydrooxazol-2-yl)benzoate were obtained.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 7.5 hours
  5. temperatureto cool
  6. washwashed with water
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was then recrystallized from methyl tert-butyl ether/ethyl acetate

Sources & evidence

ORD record
ord-b37f2f6583504af5892dd182dbf8ded7
Source dataset
uspto-grants-2015_06
Patent number
US09045465B1

Reaction notes

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