Phosphorus sulfide (P2S5) → 1,3,5-trimethyl-N-(1,1,3-trimethylindane-4-yl)pyrazole-4-carbothioamide

HRID 1904293Notes

Reaction equation

HRID 1904293 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8]([NH:10][C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]([CH3:22])[CH2:14][C:15]3([CH3:21])[CH3:20])=O)[C:4]([CH3:23])=[N:3]1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:25]>CN(C)P(N(C)C)(N(C)C)=O>[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8](=[S:25])[NH:10][C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]([CH3:22])[CH2:14][C:15]3([CH3:21])[CH3:20])[C:4]([CH3:23])=[N:3]1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 141278841,3,5-trimethyl-N-(1,1,3-trimethyl-4-indanyl)pyrazole-4-carboxamide

Product 1

HCID 145357761,3,5-trimethyl-N-(1,1,3-trimethylindane-4-yl)pyrazole-4-carbothioamideYield 128.9%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

1.1 g of 1,3,5-trimethyl-N-(1,1,3-trimethyl-4-indanyl)pyrazole-4-carboxamide, 0.79 g of phosphorus pentasulfide and 15 ml of hexamethylphosphoramide (HMPA) were stirred at 100° C. for 8 hours. After cooling, the reaction mixture was poured into ice water and extracted with ether. The extracts ether layer were dried over anhydrous magnesium sulfate and then the solvent was distilled off. The residue was chromatographed on silica gel to obtain 0.75 g of 1,3,5-trimethyl-N-(1,1,3-trimethylindane-4-yl)pyrazole-4-carbothioamide (yield 65%).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ether
  3. dry with materialThe extracts ether layer were dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-3290de5657c24c9b8029f3a58bcc13e9
Source dataset
uspto-grants-1989_06
Patent number
US04837242

Reaction notes

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