Dimethylformamide → HCID 136336910, compound

HRID 1904899Notes

Reaction equation

HRID 1904899 reaction equation
CN(C)C=O.O.[NH2:7][NH2:8].Cl([O-])(=O)(=O)=O.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:35]=[CH:36][C:37]=1[OH:38])[CH:19]=[CH:20][CH2+:21]1[C:26]2[CH:27]=[C:28]3[O:33][CH2:32][O:31][C:29]3=[CH:30][C:25]=2[CH:24]=[C:23]([CH3:34])O1>O>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:35]=[CH:36][C:37]=1[OH:38])[CH:19]=[CH:20][C:21]1[C:26]2[CH:27]=[C:28]3[O:33][CH2:32][O:31][C:29]3=[CH:30][C:25]=2[CH2:24][C:23]([CH3:34])=[N:8][N:7]=1

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 136336910HCID 136336910, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 12.5 ml of dimethylformamide and 2.1 ml (42 mM) of 100% hydrazine hydrate is cooled to 5° to 6° C. with ice-water, then 6.14 g (14 mM) of 1-(3-methoxy-4-hydroxystyryl)-3-methyl-6,7-methylenedioxy-2-benzopyrylium perchlorate (m.p. 300° C. carboniz.) are added at stirring during 15 minutes. The orange solution is stirred for a further 15 minutes, then 12.5 ml of distilled water are added at cooling which initiates the precipitation of the end-product. The crystal mash is stored for 12 hours at 5° C., filtered, washed with 3×20 ml of distilled water and dried at 80° to 100° C. Yield 4.81 g, m.p. 210° to 213° C. d. For further purification this product is refluxed with 24 ml of 99.5% ethanol, cooled, filtered, washed with 3×20 ml of ethanol and dried. Yield 4.59 g (93.7%), m.p. 214° to 216° C. (decomp.)

Workup

  1. stirringThe orange solution is stirred for a further 15 minutes
  2. temperatureat cooling which
  3. customthe precipitation of the end-product
  4. waitThe crystal mash is stored for 12 hours at 5° C.
  5. filtrationfiltered
  6. washwashed with 3×20 ml of distilled water
  7. customdried at 80° to 100° C
  8. customFor further purification this product
  9. temperatureis refluxed with 24 ml of 99.5% ethanol
  10. temperaturecooled
  11. filtrationfiltered
  12. washwashed with 3×20 ml of ethanol
  13. customdried

Sources & evidence

ORD record
ord-12d33c5b27c74866bd0e811990e911f9
Source dataset
uspto-grants-1989_06
Patent number
US04840948

Reaction notes

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