Thiosemicarbazide → HCID 58494130, compound

HRID 1942588Notes

Reaction equation

HRID 1942588 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH:12]([CH3:14])[CH3:13])[C:5](O)=O.[NH:15]([C:17](=[S:19])[NH2:18])[NH2:16]>P(Cl)(Cl)(Cl)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[S:19][C:17]([NH2:18])=[N:15][N:16]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH:12]([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 2723789ThiosemicarbazideHCID 225977283-Chloro-4-(propan-2-yloxy)benzoic acid

Product 1

HCID 58494130HCID 58494130, compoundYield 119.4%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
75 °C

Procedure

The mixture of 3-chloro-4-[(1-methylethyl)oxy]benzoic acid (5 g), hydrazinecarbothioamide (2.229 g) in phosphoric trichloride (21.43 g) was stirred at 75° C. for 3 h. Concentrated the mixture in vacuum to remove POCl3, the residue was poured into crush ice. Basified the mixture with aqueous NaOH. Extracted it with EA twice. The EA layer was concentrated in vacuum to give crude product 5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-amine (D9) (7.5 g), which was used in the next step without further purification. MS (ES): C11H12ClN3OS requires 269. found 270.1 (M+H+).

Workup

  1. concentrationConcentrated the mixture in vacuum
  2. customto remove POCl3
  3. additionthe residue was poured
  4. custominto crush ice
  5. extractionExtracted it with EA twice
  6. concentrationThe EA layer was concentrated in vacuum

Sources & evidence

ORD record
ord-1bd8e5e31f224b3795eaef07c5aee8f9
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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