Methanesulfonic Acid → HCID 14951359, compound

HRID 2211180Notes

Reaction equation

HRID 2211180 reaction equation
CS(O)(=O)=O.[NH2:6][C:7](=[S:29])[NH:8][NH:9][C:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=1>C1(C)C=CC=CC=1>[F:25][C:24]([F:27])([F:26])[C:20]1[CH:19]=[C:18]([NH:17][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:10]2[S:29][C:7]([NH2:6])=[N:8][N:9]=2)[CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 156786042-[(3-Trifluoromethylphenyl)amino]-benzoic acid, 2-(aminothioxomethyl)hydrazide

Product 1

HCID 14951359HCID 14951359, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methanesulfonic acid (260 μl, 4.01 mmoles) is added dropwise to a suspension of 2-[(3-trifluoromethylphenyl)amino]-benzoic acid, 2-(aminothioxo-methyl)hydrazide (865.9 mg, 2.44 mmoles) in 30 ml of toluene. The mixture is heated at reflux for two hours. The solvent is decanted from the bright red oil. The oil is washed with toluene and stirred with ether to yield a red solid. The solid is filtered off and suspended in 50 ml of ethyl acetate. The suspension is stirred vigorously with 10% aqueous ammonium hydroxide and the layers are separated. The ethyl acetate layer is washed with water and dried over magnesium sulfate. Filtration and concentration in vacuo gives a light brown solid that is purified by flash chromatography eluting with a gradient of hexane and ethyl acetate (1:1 to 1:3) to provide 289.5 mg (35%) of 5-[2-[(3-trifluoromethylphenyl)amino]phenyl]-1,3,4-thiadiazol-2-amine, mp 122°-123° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for two hours
  3. customThe solvent is decanted from the bright red oil
  4. washThe oil is washed with toluene
  5. customto yield a red solid
  6. filtrationThe solid is filtered off
  7. stirringThe suspension is stirred vigorously with 10% aqueous ammonium hydroxide
  8. customthe layers are separated
  9. washThe ethyl acetate layer is washed with water
  10. dry with materialdried over magnesium sulfate
  11. filtrationFiltration and concentration in vacuo
  12. customgives a light brown solid that
  13. customis purified by flash chromatography
  14. washeluting with a gradient of hexane and ethyl acetate (1:1 to 1:3)

Sources & evidence

ORD record
ord-d0916a1b8bee4f0fa106357495580dfe
Source dataset
uspto-grants-1995_10
Patent number
US05462952

Reaction notes

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