Thiosemicarbazide → HCID 66981711, compound

HRID 1942584Notes

Reaction equation

HRID 1942584 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=O)=[CH:7][C:6]=1[C:14]([F:17])([F:16])[F:15])[CH3:3].[NH:18]([C:20](=[S:22])[NH2:21])[NH2:19]>O=P(Cl)(Cl)Cl>[CH3:1][CH:2]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]2[S:22][C:20]([NH2:21])=[N:18][N:19]=2)=[CH:7][C:6]=1[C:14]([F:17])([F:16])[F:15])[CH3:3]

Participants

4

Reactant 2

HCID 2723789ThiosemicarbazideHCID 225977674-Isopropoxy-3-(trifluoromethyl)benzoic acid

Product 1

HCID 66981711HCID 66981711, compoundYield 120.3%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension 4-[(1-methylethyl)oxy]-3-(trifluoromethyl)benzoic acid (D2) (3 g) in POCl3 (11.27 mL) was added hydrazinecarbothioamide (1.652 g). The reaction mixture was heated at 90° C. for 3 h. The reaction was quenched with ice water, the pH value was adjusted to about 9 with NaOH solid. The mixture was extracted with EA/THF for 3 times. The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate and concentrated to afford 5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-amine (D3) (4.41 g). MS (ES): C12H12F3N3OS requires 303. found 304.1 (M+H+).

Workup

  1. customThe reaction was quenched with ice water
  2. extractionThe mixture was extracted with EA/THF for 3 times
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-52ebcb432d954c12a5d4df81937d463b
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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