Dimethylformamide → HCID 136114327, compound

HRID 2107819Notes

Reaction equation

HRID 2107819 reaction equation
CS[C:3]1[N:4]2[CH2:17][CH2:16][N:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:14][CH2:13][N:5]2[C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]=1.CN(C)C=O>[Zn].O>[C:18]1([N:15]2[CH2:14][CH2:13][N:5]3[C:3](=[N:8][C:7]4[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=43)[NH:4][CH2:17][CH2:16]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 14625407HCID 14625407, compound

Product 1

HCID 136114327HCID 136114327, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

A mixture of 2,3,4,5-tetrahydro-7-(methylthio)-3-phenyl-1H-[1,2,5]-triazepino[1,2-a][1,2,4]benzotriazine (0.5000 g), zinc dust (2.0 g), N,N-dimethylformamide (16 ml) and water (4 ml) was stirred magnetically and heated under reflux for 20 hours. The cooled mixture was filtered through Celite and the filter pad washed with N,N-dimethylformamide. The filtrate and washings were evaporated under oil pump vacuum to a syrup. The syrup was dissolved in dichloromethane and applied to the edges of 4 plates of Alox-100 uv254 (20×20 cm×1 mm). The plates were developed twice in dichloromethane and several times in chloroform. The major band was excised and the component eluted by stirring with methanol. The adsorbent was filtered and washed with methanol. The filtrate and washings were evaporated to a syrup. The syrup was extracted with dichloromethane and the solution was evaporated to a syrup which crystallized. The crystals were dissolved in dichloromethane and the solution was treated with charcoal and filtered through Celite. Evaporation gave a syrup which was crystallized from dichloromethane-heptane; wt. 0.127 g (30%), mp=155°-157°.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 20 hours
  3. filtrationThe cooled mixture was filtered through Celite
  4. washthe filter pad washed with N,N-dimethylformamide
  5. customThe filtrate and washings were evaporated under oil pump vacuum to a syrup
  6. dissolutionThe syrup was dissolved in dichloromethane
  7. washthe component eluted
  8. stirringby stirring with methanol
  9. filtrationThe adsorbent was filtered
  10. washwashed with methanol
  11. customThe filtrate and washings were evaporated to a syrup
  12. extractionThe syrup was extracted with dichloromethane
  13. customthe solution was evaporated to a syrup which
  14. customcrystallized
  15. dissolutionThe crystals were dissolved in dichloromethane
  16. additionthe solution was treated with charcoal
  17. filtrationfiltered through Celite
  18. customEvaporation
  19. customgave a syrup which
  20. customwas crystallized from dichloromethane-heptane

Sources & evidence

ORD record
ord-019dcd9bad3c477e96013307c73dd38f
Source dataset
uspto-grants-1990_06
Patent number
US04935515

Reaction notes

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