Dimethylformamide → HCID 20324363, compound

HRID 596941Notes

Reaction equation

HRID 596941 reaction equation
S(Cl)(Cl)=O.CN(C)C=O.[CH:10]1[C:23]2[C:22](=[O:24])[C:21]3[C:16](=[CH:17][C:18]([C:25]([NH2:27])=O)=[CH:19][CH:20]=3)[C:15](=[O:28])[C:14]=2[CH:13]=[CH:12][C:11]=1[C:29]([NH2:31])=O>O>[C:29]([C:11]1[CH:12]=[CH:13][C:14]2[C:15](=[O:28])[C:16]3[C:21](=[CH:20][CH:19]=[C:18]([C:25]#[N:27])[CH:17]=3)[C:22](=[O:24])[C:23]=2[CH:10]=1)#[N:31]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 203243689,10-Dihydro-9,10-dioxo-2,6-anthracenedicarboxamide

Product 1

HCID 20324363HCID 20324363, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Thionyl chloride (10.0 ml) was added to dimethylformamide (100 ml.) at -30° C. with stirring in 1 ml. portions. To the resulting solution, anthraquinone-2,6-dicarboxamide (4.74g.) was added in one portion and the temperature of the mixture was allowed to rise slowly to 5° C. by placing in an ice-bath. After 30 min. at this temperature, the mixture was heated over 30 min. to 65° C. The heterogeneous mixture was then poured into iced water and the solid filtered off, dried, and recrystallised from deimethylsulphoxide, 2.60g. m.p. 392° C. (decomp.) in a sealed, evacuated tube.

Workup

  1. customto rise slowly to 5° C.
  2. customby placing in an ice-bath
  3. temperaturethe mixture was heated over 30 min. to 65° C
  4. filtrationthe solid filtered off
  5. customdried
  6. customrecrystallised from deimethylsulphoxide, 2.60g
  7. customm.p. 392° C. (decomp.) in a sealed, evacuated tube

Sources & evidence

ORD record
ord-96f112e9f79e4bd9ba6650d49e9b97b2
Source dataset
uspto-grants-1977_03
Patent number
US04012500

Reaction notes

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