Hydrochloric Acid → HCID 57551240, compound

HRID 1644650Notes

Reaction equation

HRID 1644650 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([NH:12][NH2:13])=[O:11])=[CH:5][CH:4]=1.[N:16]([C:19]1[CH:24]=[CH:23][C:22]([S:25]([NH:28][C:29]2[S:30][CH:31]=[CH:32][N:33]=2)(=[O:27])=[O:26])=[CH:21][CH:20]=1)=[C:17]=S.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.N1C=CC=CC=1.Cl>O1CCCC1.C(OCC)(=O)C>[S:30]1[CH:31]=[CH:32][N:33]=[C:29]1[NH:28][S:25]([C:22]1[CH:21]=[CH:20][C:19]([NH:16][C:17]2[O:11][C:10]([CH2:9][C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:14])([F:15])[F:1])=[CH:8][CH:7]=3)=[N:12][N:13]=2)=[CH:24][CH:23]=1)(=[O:27])=[O:26]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 44674964-Isothiocyanato-N-2-thiazolylbenzenesulfonamideHCID 43237029HCID 43237029, compound

Product 1

HCID 57551240HCID 57551240, compoundYield 68.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (4-trifluoromethyl-phenyl)-acetic acid hydrazide (200 mg, 0.9 mmol, 1.0 equiv) and 4-isothiocyanato-N-thiazol-2-yl-benzenesulfonamide (273 mg, 0.9 mmol, 1.0 equiv) in 3 mL of anhydrous tetrahydrofuran was stirred at ambient temperature. After 18 h, p-toluenesulfonyl chloride (210 mg, 1.1 mmol, 1.2 equiv) and pyridine (156 mL, 1.93 mmol, 2.10 equiv) were added, and the reaction mixture was heated at reflux. After 4 h, the reaction mixture was cooled to ambient temperature. Ethyl acetate (3 mL) and 1 N hydrochloric acid (3 mL) were added. After stirring vigorously for 5 min, the layers were separated. The aqueous layer was extracted with ethyl acetate (3 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was triturated with hot acetonitrile to afford the product as a light yellow solid (295 mg, 60%).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux
  3. waitAfter 4 h
  4. temperaturethe reaction mixture was cooled to ambient temperature
  5. stirringAfter stirring vigorously for 5 min
  6. customthe layers were separated
  7. extractionThe aqueous layer was extracted with ethyl acetate (3 mL)
  8. dry with materialThe combined organic layers were dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was triturated with hot acetonitrile

Sources & evidence

ORD record
ord-6f765940a1ab4f2998a167ad9a1f77fe
Source dataset
uspto-grants-2012_02
Patent number
US08124610B2

Reaction notes

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