Diethylformamide → HCID 13345879, compound

HRID 745663Notes

Reaction equation

HRID 745663 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[C:14]([CH:15]=1)=[N:13][C:12]([N:16]([CH3:18])[CH3:17])=[C:11]1[C:6]=2[CH:7]=[CH:8][C:9]([NH2:19])=[CH:10]1.P(Cl)(Cl)(Cl)=O.[CH2:25]([N:27]([CH2:30][CH3:31])[CH:28]=O)[CH3:26]>CC(C)=O>[CH2:25]([N:27]([CH:28]=[N:1][C:2]1[CH:3]=[CH:4][C:5]2[C:14]([CH:15]=1)=[N:13][C:12]([N:16]([CH3:17])[CH3:18])=[C:11]1[C:6]=2[CH:7]=[CH:8][C:9]([N:19]=[CH:28][N:27]([CH2:30][CH3:31])[CH2:25][CH3:26])=[CH:10]1)[CH2:30][CH3:31])[CH3:26]

Participants

5

Reactant 3

HCID 12051Diethylformamide2×HCID 24813Phosphorus oxychlorideHCID 23314008HCID 23314008, compound

Product 1

HCID 13345879HCID 13345879, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 3,8-diamino-6-dimethylaminophenanthridine (500 mg) in N,N-diethylformamide (2 ml) was added to a mixture of phosphorus oxychloride (1.5 ml) and N,N-diethylformamide (5 ml), the temperature of the mixture being kept at 5° C. The resulting mixture was stirred for 30 minutes at room temperature, heated at 75°-80° C. for 2 hours, cooled, and diluted with acetone. The precipitate formed was filtered off and dissolved in water. The pH of the clear solution was adjusted to a value of 9 with aqueous ammonia. The solid thus obtained was filtered off, washed with water, dried, and purified by column chromatography over a neutral aluminum oxide column using benzene as the mobile phase. The product crystallized out from chloroform/diisopropyl ether. Yield 71%, melting point 124°-126° C.

Workup

  1. custombeing kept at 5° C
  2. temperatureheated at 75°-80° C. for 2 hours
  3. temperaturecooled
  4. customThe precipitate formed
  5. filtrationwas filtered off
  6. dissolutiondissolved in water
  7. customThe solid thus obtained
  8. filtrationwas filtered off
  9. washwashed with water
  10. customdried
  11. custompurified by column chromatography over a neutral aluminum oxide column
  12. customThe product crystallized out from chloroform/diisopropyl ether

Sources & evidence

ORD record
ord-0d33105694e148319a73c29543e2b04d
Source dataset
uspto-grants-1986_07
Patent number
US04599409

Reaction notes

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