Methanesulfonic Acid → HCID 17603799, compound

HRID 351555Notes

Reaction equation

HRID 351555 reaction equation
[CH2:1]([O:6][C:7]1[CH:19]=[CH:18][C:10]([C:11]([NH:13][NH:14][C:15]([NH2:17])=[S:16])=O)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5].CS(O)(=O)=O>C1(C)C=CC=CC=1>[NH2:17][C:15]1[S:16][C:11]([C:10]2[CH:18]=[CH:19][C:7]([O:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:8][CH:9]=2)=[N:13][N:14]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 22713213HCID 22713213, compound

Product 1

HCID 17603799HCID 17603799, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
10 °C

Procedure

To a slurry of 1-(4-n-pentyloxybenzoyl)-3-thiosemicarbazide (20 g) in toluene (213.3 ml) at 40° C., was added dropwise over 30 minutes, methanesulfonic acid (6.92 ml). The mixture was refluxed for 12 hours. After cooling to 10° C, the resulting precipitate was filtered and dried. The precipitate was dissolved in water, the solution was adjusted to pH 9 with 1N sodium hydroxide and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated under reduced pressure to give 2-amino-5-(4-n-pentyloxyphenyl)-1,3,4-thiadiazole (4.314 g).

Workup

  1. temperatureThe mixture was refluxed for 12 hours
  2. filtrationthe resulting precipitate was filtered
  3. customdried
  4. dissolutionThe precipitate was dissolved in water
  5. extractionextracted with ethyl acetate
  6. customThe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried over magnesium sulfate
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c1e4beffe13541c293648e2268225b97
Source dataset
uspto-grants-2004_06
Patent number
US06743776B2

Reaction notes

Loading…