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

HRID 1051432Notes

Reaction equation

HRID 1051432 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[N:8]=[CH:9][S:10][C:11]=2[NH:12][C:13](=O)[CH3:14])[CH:6]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>P(Cl)(Cl)(Cl)=O>[CH3:14][C:13]1[C:6]2[N:5]([CH:4]=[N:3][C:2]=2[CH3:1])[C:7]2[N:8]=[CH:9][S:10][C:11]=2[N:12]=1

Participants

4

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 86715562N-(4-(4-methyl-1H-imidazol-1-yl)thiazol-5-yl)acetamide

Product 1

HCID 734258605,6-Dimethyl-3-thia-1,4,7,8a-tetraaza-as-indaceneYield 33%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
160 °C

Procedure

N-(4-(4-methyl-1H-imidazol-1-yl)thiazol-5-yl)acetamide (50 mg, 0.23 mmol) was suspended in phosphorus oxychloride (5 mL) and P2O5 (326 mg, 2.3 mmol) was added quickly. The resulting mixture was heated at 160° C. in a sealed tube for 24 hr. 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. The organic layer was dried over Na2SO4, concentrated (the crude product can also be directly used for next step), purified by prep-HPLC to give 15 mg of the title compound (yield: 33%).

Workup

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

Sources & evidence

ORD record
ord-08d9e5e42db7421891553a097faec604
Source dataset
uspto-grants-2016_07
Patent number
US09388180B2

Reaction notes

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