Ammonia → HCID 23465073, compound

HRID 443721Notes

Reaction equation

HRID 443721 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[C:13]([C:14](Cl)=[O:15])=[CH:12][S:11][N:10]=2)[CH:4]=1.[NH3:19]>C1COCC1>[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[C:13]([C:14]([NH2:19])=[O:15])=[CH:12][S:11][N:10]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 23465058HCID 23465058, compound

Product 1

HCID 23465073HCID 23465073, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2.92 g (0.010 mol) of 3-(α,α,α-trifluoro-m-tolyl)-4-isothiazolecarbonyl chloride in 10 ml of THF was added to a solution of excess ammonia gas in THF stirred in a dry ice acetone bath. The mixture was slowly warmed to 23° with stirring. The solid NH4Cl was removed by filtration, and the filtrate was concentrated to about 20 ml. Then 100 ml of ether was added, and the solution was extracted with two portions of 10% Na2CO3 solution and once with saturated NaCl solution. The ether layer was dried (CaSO4) and concentrated to 2.25 g (83%) of white solid, m.p. 141°-141.5°; infrared (mineral oil mull) 2.92, 3.11, 6.09, 6.11μ.

Workup

  1. temperatureThe mixture was slowly warmed to 23°
  2. stirringwith stirring
  3. customThe solid NH4Cl was removed by filtration
  4. concentrationthe filtrate was concentrated to about 20 ml
  5. additionThen 100 ml of ether was added
  6. extractionthe solution was extracted with two portions of 10% Na2CO3 solution and once with saturated NaCl solution
  7. dry with materialThe ether layer was dried (CaSO4)
  8. concentrationconcentrated to 2.25 g (83%) of white solid, m.p. 141°-141.5°

Sources & evidence

ORD record
ord-c299489c8739434aa3361f2f3d8765c3
Source dataset
uspto-grants-1981_04
Patent number
US04261728

Reaction notes

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