Triethylamine → HCID 131718038, compound

HRID 2253763Notes

Reaction equation

HRID 2253763 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[C:15]([C:22](O)=[S:23])=[N:14]1.C(N(CC)CC)C.C1(P([N:46]=[N+:47]=[N-:48])(C2C=CC=CC=2)=O)C=CC=CC=1>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[C:15]([C:22]([N:46]=[N+:47]=[N-:48])=[S:23])=[N:14]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 178526154HCID 178526154, compound

Product 1

HCID 131718038HCID 131718038, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
5 °C

Procedure

1-(2,6-Dichloro-4-trifluoromethylphenyl)-4-trifluoromethylthiopyrazole-3-carboxylic acid (5.6 g) was dissolved in dry N,N-dimethylformamide (50 ml) and triethylamine (1.33 g) added. After cooling to 5° C., a solution of diphenylphosphorylazide (3.63 g) in N,N-dimethylformamide (20 ml) was added. When the solution had reached ambient temperature, it was heated to 35° C. for 21/2 hours. After evaporation in vacuo at a temperature kept below 40° C., a solution of sodium chloride (5 g) in water (100 ml) was added, and the suspension extracted with ether (3×100 ml). The combined extracts were washed with water (50 ml), dried over anhydrous magnesium sulphate and evaporated to give 1-(2,6-dichloro-4-trifluoromethylphenyl)4-trifluoromethylthiopyrazole-3-carboxylic acid azide (5.4 g). A solution of this in dry toluene (200 ml) was heated under reflux with stirring for 1.5 hours, tert-butanol (35 ml) was added, and reflux continued for 4 hours. After evaporation in vacuo the residue was purified by chromatography eluting with dichloromethane to give the title compound (3.3 g) as an off-white solid, m.p. 122°-125° C.

Workup

  1. customhad reached ambient temperature
  2. temperatureit was heated to 35° C. for 21/2 hours
  3. customAfter evaporation in vacuo at a temperature
  4. customkept below 40° C.
  5. additiona solution of sodium chloride (5 g) in water (100 ml) was added
  6. extractionthe suspension extracted with ether (3×100 ml)
  7. washThe combined extracts were washed with water (50 ml)
  8. dry with materialdried over anhydrous magnesium sulphate
  9. customevaporated

Sources & evidence

ORD record
ord-130c9c323d544127b1980c0a292ad06e
Source dataset
uspto-grants-1993_08
Patent number
US05232940

Reaction notes

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