Phosphorus sulfide (P2S5) → HCID 86663792, compound

HRID 570954Notes

Reaction equation

HRID 570954 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[N:6]2[CH:9]=[N:10][C:11]([C:12]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=O)=[C:5]2[N:4]=[N:3]1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:22].C[Si](C)(C)O[Si](C)(C)C>C(Cl)Cl>[CH3:1][N:2]1[C:7](=[O:8])[N:6]2[CH:9]=[N:10][C:11]([C:12](=[S:22])[NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:5]2[N:4]=[N:3]1

Participants

5

Reactant 3

HCID 14817Phosphorus sulfide (P2S5)HCID 24764HexamethyldisiloxaneHCID 49869278HCID 49869278, compound

Product 1

HCID 86663792HCID 86663792, compoundYield 270.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-methyl-4-oxo-N-phenyl-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide (430 mg, 1.59 mmol), phosphorus pentasulfide (212 mg, 0.48 mmol) and hexamethyldisiloxane (680 μL, 3.18 mmol) in DCM (20 mL) was refluxed overnight. The crude product was absorbed on silica and was purified by flash chromatography using a gradient elution of DCM:MeOH (100:0 to 98:2) to give 372 mg of 3-methyl-4-oxo-N-phenyl-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carbothioamide as a 1.5:1 inseparable mixture with the starting material.

Workup

  1. temperaturewas refluxed overnight
  2. customThe crude product was absorbed on silica
  3. customwas purified by flash chromatography
  4. washa gradient elution of DCM:MeOH (100:0 to 98:2)

Sources & evidence

ORD record
ord-68770f884d1f4ec9b678718ff4dc0597
Source dataset
uspto-grants-2015_05
Patent number
US09024018B2

Reaction notes

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