Dimethylformamide → HCID 20474277, compound

HRID 2295899Notes

Reaction equation

HRID 2295899 reaction equation
[C:1]([NH:4][C:5]1[C:6](=[O:23])[O:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([N:15]1[N:19]=[C:18]([CH2:20][CH3:21])[C:17]([CH3:22])=[N:16]1)[CH:9]=2)(=O)C.P(Cl)(Cl)(Cl)=O.[CH3:29][N:30](C)[CH:31]=O>>[CH3:29][N:30]([CH:1]=[N:4][C:5]1[C:6](=[O:23])[O:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([N:15]1[N:19]=[C:18]([CH2:20][CH3:21])[C:17]([CH3:22])=[N:16]1)[CH:9]=2)[CH3:31]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 20474287HCID 20474287, compound

Product 1

HCID 20474277HCID 20474277, compoundYield 80%

Procedure

15.6 g (50.0 mmols) of 3-acetylamino-7-(4-ethyl-5-methyl-2H-1,2,3-triazol-2-yl)-coumarin are suspended in 100 ml of anhydrous dimethylformamide. 11.5 g (75.0 mmols) of phosphorus oxychloride are added dropwise to the suspension at 10°-15° C., and the mixture is stirred for 22 hours at room temperature. The slurry is introduced into 500 ml of ice water, and the mixture is filtered and brought to a pH of 8 with sodium carbonate. The yellow crystals are filtered off under suction, washed with water and dried: 15.5 g (95.5%). Recrystallisation from ethanol yields 12.9 g (80%) of 3-(dimethylaminomethyleneamino)-7-(4-ethyl-5-methyl-2H-1,2,3-triazol-2-yl)-coumarin in the form of small pale yellow crystals of melting point 158°-159° C.

Workup

  1. filtrationthe mixture is filtered
  2. filtrationThe yellow crystals are filtered off under suction
  3. washwashed with water
  4. customdried
  5. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-8b2f10eafef14866a3546df98defcaa7
Source dataset
uspto-grants-1984_01
Patent number
US04426530

Reaction notes

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