Tert-Butyl nitrite → HCID 22466148, compound

HRID 1934313Notes

Reaction equation

HRID 1934313 reaction equation
N(OC(C)(C)C)=O.[Cl:8][C:9]1[CH:15]=[C:14]([F:16])[C:13]([C:17]2[C:22]([Cl:23])=[CH:21][C:20]([C:24]([F:27])([F:26])[F:25])=[CH:19][N:18]=2)=[CH:12][C:10]=1[NH2:11].[N-:28]=[N+:29]=[N-].[Na+]>FC(F)(F)C(O)=O>[Cl:8][C:9]1[CH:15]=[C:14]([F:16])[C:13]([C:17]2[C:22]([Cl:23])=[CH:21][C:20]([C:24]([F:26])([F:27])[F:25])=[CH:19][N:18]=2)=[CH:12][C:10]=1[N:11]=[N+:28]=[N-:29]

Participants

5

Reactant 3

HCID 10906Tert-Butyl nitrite2×HCID 33557Sodium AzideHCID 11131164HCID 11131164, compound

Product 1

HCID 22466148HCID 22466148, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent2×

Procedure

With ice-cooling, initially 9.5 g (92 mmol) of tert-butyl nitrite were added dropwise to a solution of 20 g (62 mmol) of 2-chloro-5-(3-chloro-5-trifluoromethyl-2-pyridyl)-4-fluoroaniline in 40 ml of trifluoroacetic acid, and—with strong evolution of gas—6 g (92 mmol) of sodium azide were then added a little at a time. The mixture was stirred for 16 hours, and a further 15 ml of trifluoroacetic acid and 1.7 g (17 mmol) of tert-butyl nitrite were then added to the reaction mixture. Stirring was subsequently continued for another 30 minutes, and the mixture was then poured onto 0.3 l of ice-water. The resulting solid fraction was separated off and washed with 50 ml of water. For purification, the crude product was initially dissolved in 100 ml of toluene. The resulting toluene phase was then washed with saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate and finally concentrated. Yield: 90%;

Workup

  1. temperatureWith ice-cooling
  2. stirringStirring
  3. waitwas subsequently continued for another 30 minutes
  4. customThe resulting solid fraction was separated off
  5. washwashed with 50 ml of water
  6. customFor purification
  7. dissolutionthe crude product was initially dissolved in 100 ml of toluene
  8. washThe resulting toluene phase was then washed with saturated aqueous sodium bicarbonate solution
  9. dry with materialdried over magnesium sulfate
  10. concentrationfinally concentrated

Sources & evidence

ORD record
ord-67f327fee3944433af4682903b7060c1
Source dataset
uspto-grants-2002_05
Patent number
US06383986B1

Reaction notes

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