Methanesulfonic Acid → 5-(4-butoxyphenyl)-1,3,4-thiadiazol-2-amine

HRID 1977268Notes

Reaction equation

HRID 1977268 reaction equation
[CH2:1]([O:5][C:6]1[CH:18]=[CH:17][C:9]([C:10]([NH:12][NH:13][C:14]([NH2:16])=[S:15])=O)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].CS(O)(=O)=O>C1(C)C=CC=CC=1>[NH2:16][C:14]1[S:15][C:10]([C:9]2[CH:17]=[CH:18][C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:7][CH:8]=2)=[N:12][N:13]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 1674586HCID 1674586, compound

Product 1

HCID 6596605-(4-butoxyphenyl)-1,3,4-thiadiazol-2-amineYield 23.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
10 °C

Procedure

To a slurry of 1-(4-n-butyloxybenzoyl)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 stirred under refluxing for 12 hours. After cooling to 10° C., the sulfonate salt was filtered and dried. The salt was placed 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-butyloxyphenyl)-1,3,4-thiadiazole (4.314 g).

Workup

  1. temperatureunder refluxing for 12 hours
  2. filtrationthe sulfonate salt was filtered
  3. customdried
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c5bd995d42fe45488d3477224b304bb8
Source dataset
uspto-grants-2001_05
Patent number
US06232290B1

Reaction notes

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