Phosphorus oxide (P4O10) → 2,5,6-Trimethyl-8-propyl-3-thia-1,4,7,8a-tetraaza-as-indacene

HRID 1051428Notes

Reaction equation

HRID 1051428 reaction equation
[CH3:1][C:2]1[S:3][C:4]([NH:16][C:17](=O)[CH3:18])=[C:5]([N:7]2[CH:11]=[C:10]([CH3:12])[N:9]=[C:8]2[CH2:13][CH2:14][CH3:15])[N:6]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>P(Cl)(Cl)(Cl)=O>[CH3:1][C:2]1[S:3][C:4]2[N:16]=[C:17]([CH3:18])[C:11]3[N:7]([C:8]([CH2:13][CH2:14][CH3:15])=[N:9][C:10]=3[CH3:12])[C:5]=2[N:6]=1

Participants

4

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 86715560N-(2-methyl-4-(4-methyl-2-propyl-1H-imidazol-1-yl)thiazol-5-yl)acetamide

Product 1

HCID 734259722,5,6-Trimethyl-8-propyl-3-thia-1,4,7,8a-tetraaza-as-indaceneYield 7.7%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
130 °C

Procedure

N-(2-methyl-4-(4-methyl-2-propyl-1H-imidazol-1-yl)thiazol-5-yl)acetamide (60 mg, 0.2 mmol) was suspended in phosphorus oxychloride (5 mL) and P2O5 (280 mg, 2 mmol) was added quickly. The resulting mixture was heated at 130° C. in a sealed tube overnight. After POCl3 was evaporated, the residue was quenched with ice water very carefully. The mixture was neutralized with saturated Na2CO3 solution and extracted with ethyl acetate (3×30 mL). The organic layer was dried over Na2SO4, concentrated and purified by prep-HPLC to give 4 mg of the title compound.

Workup

  1. customAfter POCl3 was evaporated
  2. customthe residue was quenched with ice water very carefully
  3. extractionextracted with ethyl acetate (3×30 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-1bff24cc3e2d41dd8e75b5bdcf45176d
Source dataset
uspto-grants-2016_07
Patent number
US09388180B2

Reaction notes

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