Acetic Acid → HCID 178433853, compound

HRID 2295903Notes

Reaction equation

HRID 2295903 reaction equation
[Cl-:1].[CH3:2][N+:3]1[N:4]=[CH:5][N:6]([CH2:8][C:9]#N)[CH:7]=1.[OH:11][C:12]1[CH:19]=[C:18]([N:20]2[N:24]=[C:23]([CH3:25])[C:22]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:21]2)[CH:17]=[CH:16][C:13]=1[CH:14]=O.C(O)(=[O:34])C>CN(C)C=O>[Cl-:1].[CH3:2][N+:3]1[N:4]=[CH:5][N:6]([C:8]2[C:9](=[O:34])[O:11][C:12]3[C:13]([CH:14]=2)=[CH:16][CH:17]=[C:18]([N:20]2[N:24]=[C:23]([CH3:25])[C:22]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)=[N:21]2)[CH:19]=3)[CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 12412923HCID 12412923, compoundHCID 178481280HCID 178481280, compound

Product 1

HCID 178433853HCID 178433853, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.48 g (22.0 mmols) of 1-methyl-4-cyanomethyl-1,2,4-triazolium chloride are added to 6.02 g (20.0 mmols) of the Na salt of 2-hydroxy-4-(4-methyl-5-phenyl-2H-1,2,3-triazol-2-yl)-benzaldehyde and 4.80 g (80.0 mmols) of glacial acetic acid in 20 ml of anhydrous dimethylformamide, under an N2 atmosphere, and the mixture is stirred for 24 hours at room temperature. The precipitate is filtered off under suction, washed with dimethylformamide and dried: 3.60 g (43%) of a pale yellow powder. Recrystallisation from water yields 2.90 g (35%) of 1-methyl-4-[7-(4-methyl-5-phenyl-2H-1,2,3-triazol-2-yl)-coumarin-3-yl]-1,2,4-triazolium chloride in the form of small pale yellow crystals of melting point 249°-252° C. (decomposition).

Workup

  1. filtrationThe precipitate is filtered off under suction
  2. washwashed with dimethylformamide
  3. customdried
  4. customRecrystallisation from water

Sources & evidence

ORD record
ord-fe66a0cec02245c0bccd41dbc64424bc
Source dataset
uspto-grants-1984_01
Patent number
US04426530

Reaction notes

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