Trifluoroacetic acid → HCID 22492898, compound

HRID 1816351Notes

Reaction equation

HRID 1816351 reaction equation
[CH:1]1([N:7]2[CH2:12][CH2:11][CH:10]([C:13]3[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=3)[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N[NH:22][C:23]([NH2:25])=[S:24].[F:26][C:27]([F:32])([F:31])[C:28]([OH:30])=[O:29]>C1(C)C=CC=CC=1>[F:26][C:27]([F:32])([F:31])[C:28]([OH:30])=[O:29].[CH:1]1([N:7]2[CH2:8][CH2:9][CH:10]([C:13]3[CH:14]=[CH:15][C:16]([C:17]4[S:24][C:23]([NH2:25])=[N:22][N:18]=4)=[CH:19][CH:20]=3)[CH2:11][CH2:12]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 2723789ThiosemicarbazideHCID 22492892HCID 22492892, compound

Product 1

HCID 22492898HCID 22492898, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4-(1-cyclohexyl-4-piperidyl)benzonitrile (0.68 g), thiosemicarbazide (0.58 g) and trifluoroacetic acid (3.5 ml) in toluene (7 ml) was stirred for 7 hours at 70° C. After being cooled to room temperature, the solvent was evaporated in vacuo. Then the residue was dissolved in tetrahydrofuran and poured into water. The solution was adjusted to pH 8 with 1N aqueous sodium hydroxide. The resulting precipitate was collected by filtration and washed with water and isopropyl ether to give 5-[4-(1-cyclohexyl-4-piperidyl)phenyl]-1,3,4-thiadiazol-2-amine trifluroacetate (0.80 g).

Workup

  1. temperatureAfter being cooled to room temperature
  2. customthe solvent was evaporated in vacuo
  3. dissolutionThen the residue was dissolved in tetrahydrofuran
  4. additionpoured into water
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with water and isopropyl ether

Sources & evidence

ORD record
ord-a4cd9676a2ef4d1880f47db8c6c01c5c
Source dataset
uspto-grants-2005_04
Patent number
US06884774B2

Reaction notes

Loading…