Water → HCID 21220291, compound

HRID 1584806Notes

Reaction equation

HRID 1584806 reaction equation
[F:1][C:2]1[C:12]([CH3:13])=[C:11](F)[C:10]([F:15])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[N-:16]=[N+:17]=[N-:18].[Na+].C(OCC)(=O)C.O>CS(C)=O>[N:16]([C:11]1[C:10]([F:15])=[CH:9][C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[C:2]([F:1])[C:12]=1[CH3:13])=[N+:17]=[N-:18]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 21220461Ethyl 2,4,5-trifluoro-3-methylbenzoate

Product 1

HCID 21220291HCID 21220291, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
55 °C

Procedure

In 308 ml of dimethyl sulfoxide was dissolved 61.7 g of ethyl 2,4,5-trifluoro-3-methylbenzoate, and 42.3 g of sodium azide was added to the solution, after which the resulting mixture was stirred at 55° C. for 14 hours. The reaction mixture was cooled to room temperature and thereafter added to a mixed solvent of 500 ml of ethyl acetate and 1200 ml of water. The organic layer formed was separated, washed with water and then dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure to obtain 65.3 g of pale yellow, oily ethyl 4-azido-2,5-difluoro-3-methylbenzoate.

Workup

  1. additionwas added to the solution
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customThe organic layer formed
  4. customwas separated
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was then removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-0a111ce15a4c49e78ee5bd5280ce84e0
Source dataset
uspto-grants-1999_08
Patent number
US05935952

Reaction notes

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