Dimethylformamide → HCID 178441001, compound

HRID 268277Notes

Reaction equation

HRID 268277 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:26]>C(O)(C)C>[OH2:26].[ClH:1].[Cl:1][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][C:6]=1[CH2:8][CH2:3][CH2:4][CH3:5])[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.[Cl:1][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][C:6]=1[CH2:18][CH2:9][CH2:10][CH3:11])[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.[ClH:1]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 178428198HCID 178428198, compound

Product 1

HCID 178441001HCID 178441001, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
110 °C

Procedure

A 500 ml. 3-neck, r.b. flask fitted with stirrer, condenser and thermometer was charged with the remainder of the filtrate from part A, the compound of Example I, C.(20.9 g. 0.0962 mole) and an additional 100 ml. dimethylformamide. The mixture was stirred overnight while heating at 110°C. The solution was chilled and the crystals were collected by filtration and dried at 60°C to yield 23 g. off white crystals, m.p. 260°- 268°C. The filtrate was concentrated to 150 ml. by rotary evapaorator and chilled. Crop II was collected and dried to yield 3.9 g. light yellow crystals, m.p. 238°-251°C. Both crops were dissolved in isopropanol (600 ml.) and filtered while hot. The filtrate was chilled and the crystals were collected and dried at 60°C to yield 13.2 g. light yellow crystals, m.p. 273°-276°C.

Workup

  1. customflask fitted with stirrer, condenser
  2. temperatureThe solution was chilled
  3. filtrationthe crystals were collected by filtration
  4. customdried at 60°C
  5. customto yield 23 g
  6. concentrationThe filtrate was concentrated to 150 ml
  7. temperatureby rotary evapaorator and chilled
  8. customCrop II was collected
  9. customdried
  10. customto yield 3.9 g
  11. filtrationfiltered while hot
  12. temperatureThe filtrate was chilled
  13. customthe crystals were collected
  14. customdried at 60°C
  15. customto yield 13.2 g

Sources & evidence

ORD record
ord-720eb561ab3143b8882ba783059d8e43
Source dataset
uspto-grants-1976_03
Patent number
US03947434

Reaction notes

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