Isopropanol → HCID 178436566, compound

HRID 268276Notes

Reaction equation

HRID 268276 reaction equation
[ClH:1].[NH:2]([C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]3[N:21]=[CH:20][NH:19][C:17]3=2)[N:12]=[C:11]([CH3:22])[CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CN(C)C=O.[CH:28](O)([CH3:30])C>>[ClH:1].[Cl:1][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][C:6]=1[CH2:28][CH3:30])[NH:2][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]3[N:21]=[CH:20][NH:19][C:17]3=2)[N:12]=[C:11]([CH3:22])[CH:10]=1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 6228DimethylformamideHCID 178428198HCID 178428198, compound

Product 1

HCID 178436566HCID 178436566, compound

Procedure

A 500 ml. 3-neck, r.b. flask fitted with stirrer, condenser and thermometer was charged with the filtrate from Part A, the compound of Example I, C. (44.3 g. 0.204 mole) and an additional 100 ml. dimethylformamide and the mixture was heated at reflux overnight while stirring. The near solution was chilled and the crystals were collected by filtration. The solid was washed with ether (ca. 300 ml.). Crop I was dried at 60°C to yield 46.8 g. straw colored crystals, m.p. 258°-272°C. The ether filtrate was concentrated to near dryness and chilled. Crop II was collected and dried to yield 7.2 g. tan crystals, m.p. 256°-270°C. The reaction filtrate was concentrated to about 200 ml. diluted with ether (100 ml.) and chilled. Crop III was collected and dried to yield 6.8 g. tan crystals, m.p. 120°-130°C. The crude product (Crops, I, II and III) was dissolved in isopropanol (ca. 2800 ml.) and filtered while hot. The filtrate was chilled and the crystals collected by filtration and dried at 60°C to yield 25.3 g. light yellow crystals, m.p. 283°-287° C. The filtrae was concentrated to 1400 ml. by rotary evaporator and chilled. The crystals were collected and dried to yield 8.9 g. light yellow crystals, m.p. 282°-287°C.

Workup

  1. customflask fitted with stirrer, condenser
  2. additionthermometer was charged with the filtrate from Part A
  3. temperatureat reflux overnight
  4. temperatureThe near solution was chilled
  5. filtrationthe crystals were collected by filtration
  6. washThe solid was washed with ether (ca. 300 ml.)
  7. customCrop I was dried at 60°C
  8. customto yield 46.8 g
  9. concentrationThe ether filtrate was concentrated
  10. temperaturechilled
  11. customCrop II was collected
  12. customdried
  13. customto yield 7.2 g
  14. concentrationThe reaction filtrate was concentrated to about 200 ml
  15. additiondiluted with ether (100 ml.)
  16. temperaturechilled
  17. customCrop III was collected
  18. customdried
  19. customto yield 6.8 g
  20. filtrationfiltered while hot
  21. temperatureThe filtrate was chilled
  22. filtrationthe crystals collected by filtration
  23. customdried at 60°C
  24. customto yield 25.3 g
  25. concentrationThe filtrae was concentrated to 1400 ml
  26. customby rotary evaporator
  27. temperaturechilled
  28. customThe crystals were collected
  29. customdried
  30. customto yield 8.9 g

Sources & evidence

ORD record
ord-4195dcfa46224fd48d1c8047e46f3caf
Source dataset
uspto-grants-1976_03
Patent number
US03947434

Reaction notes

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