Dimethyl Sulfoxide → 1-(Azidomethyl)-3,5-bis(trifluoromethyl)benzene

HRID 1620796

Reaction equation

HRID 1620796 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].CS(C)=O.[F:9][C:10]([F:24])([F:23])[C:11]1[CH:12]=[C:13]([CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=1)[CH2:14]Cl>O>[N:1]([CH2:14][C:13]1[CH:16]=[C:17]([C:19]([F:21])([F:22])[F:20])[CH:18]=[C:11]([C:10]([F:9])([F:23])[F:24])[CH:12]=1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 679Dimethyl Sulfoxide2×HCID 33557Sodium AzideHCID 1235761-(Chloromethyl)-3,5-bis(trifluoromethyl)benzene2×

Product 1

HCID 441857431-(Azidomethyl)-3,5-bis(trifluoromethyl)benzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

Sodium azide (74.3 g, 1.14 mol) is suspended in water (125 mL), then DMSO (625 mL) is added. After stirring for 30 minutes, a solution consisting of 3,5-Bis(trifluoromethyl)benzyl chloride (255.3 g, 0.97 moles) and DMSO (500 mL) is added over 30 minutes. (The 3,5-Bis(trifluoromethyl)benzyl chloride is heated to 35° C. to liquefy prior to dispensing (MP=30-32° C.)). The benzyl chloride feed vessel is rinsed with DMSO (50 mL) into the sodium azide solution, the mixture is heated to 40° C., and then maintained for an hour at 40° C., then cooled to 23° C.

Workup

  1. additionis added over 30 minutes
  2. washThe benzyl chloride feed vessel is rinsed with DMSO (50 mL) into the sodium azide solution
  3. temperaturemaintained for an hour at 40° C.
  4. temperaturecooled to 23° C.

Sources & evidence

ORD record
ord-ac037c254dfd47ffaab08cedc7a253c6
Source dataset
uspto-grants-2014_07
Patent number
US08772496B2

Linked notes

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