Triethylamine hydrochloride → HCID 23131657, compound

HRID 1180717Notes

Reaction equation

HRID 1180717 reaction equation
[C:1]1([N:11]=[C:12](Cl)[C:13]([F:16])([F:15])[F:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[N-:18]=[N+:19]=[N-:20].[Na+].Cl.C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:1]1([N:11]2[C:12]([C:13]([F:16])([F:15])[F:14])=[N:20][N:19]=[N:18]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 10332712143681-37-2

Product 1

HCID 23131657HCID 23131657, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Four grams (15.5 mmol) of N-(naphthalen-1-yl)-2,2,2-trifluoroacetimidoyl chloride obtained in Example 13, 1.84 g (27.9 mmol) of sodium azide, 1.08 g (7.76 mmol) of triethylamine hydrochloride, and 40 ml of toluene were introduced into a 100 ml flask and reacted at 80° C. for 14 hours. After the reaction, the reaction solution was cooled to room temperature and washed with water (30 ml×2). The organic phase was dried over anhydrous magnesium sulfate for 1 hour, filtered, and then subjected to solvent removal by evaporation. The crude product thus obtained was precipitated for 1 hour in 18 ml of n-hexane while being cooled using an ice bath, followed by filtration and drying, thereby giving 3.86 g of 1-(naphthalen-1-yl)-5-(trifluoromethyl)-1H-tetrazole as a white powder (yield: 94.1%).

Workup

  1. customreacted at 80° C. for 14 hours
  2. customAfter the reaction
  3. washwashed with water (30 ml×2)
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate for 1 hour
  5. filtrationfiltered
  6. customsubjected to solvent removal by evaporation
  7. customThe crude product thus obtained
  8. customwas precipitated for 1 hour in 18 ml of n-hexane
  9. temperaturewhile being cooled
  10. filtrationfollowed by filtration
  11. customdrying

Sources & evidence

ORD record
ord-e1c5ede3723f45bcbe00f0758fa6f99c
Source dataset
uspto-grants-2007_10
Patent number
US07282609B2

Reaction notes

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