Thiosemicarbazide → HCID 66981824, compound

HRID 1942602Notes

Reaction equation

HRID 1942602 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[CH2:12][CH:13]([CH3:15])[CH3:14])[C:6](O)=O)#[N:2].[NH:16]([C:18](=[S:20])[NH2:19])[NH2:17]>O=P(Cl)(Cl)Cl>[NH2:19][C:18]1[S:20][C:6]([C:5]2[CH:9]=[CH:10][C:11]([CH2:12][CH:13]([CH3:15])[CH3:14])=[C:3]([CH:4]=2)[C:1]#[N:2])=[N:17][N:16]=1

Participants

4

Reactant 2

HCID 2723789ThiosemicarbazideHCID 222281753-Cyano-4-isobutylbenzoic acid

Product 1

HCID 66981824HCID 66981824, compoundYield 113%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension 3-cyano-4-(2-methylpropyl)benzoic acid (D24) (305 mg) in POCl3 (2 mL) was added hydrazinecarbothioamide (211 mg). The reaction mixture was heated at 90° C. for 3 h. The reaction was quenched with ice water. NaOH solid was added until Ph=8-9. The mixture was extracted with EA/THF for 3 times. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate. The dried solution was concentrated to afford the 5-(5-amino-1,3,4-thiadiazol-2-yl)-2-(2-methylpropyl)benzonitrile (D25) (438 mg), which was used for the next step without further purification. MS (ES): C13H14N4S requires 258. found 259.1 (M+H+).

Workup

  1. customThe reaction was quenched with ice water
  2. additionNaOH solid was added until Ph=8-9
  3. extractionThe mixture was extracted with EA/THF for 3 times
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe dried solution was concentrated

Sources & evidence

ORD record
ord-dc8b34ff56bb47a7985e72ece2dc845e
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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