Chloroacetaldehyde → N,N-Diethyl-2-{9-[2-(1,3-thiazol-2-yl)hydrazinylidene]acridin-10(9H)-yl}ethan-1-amine--hydrogen chloride (1/2)

HRID 986254Notes

Reaction equation

HRID 986254 reaction equation
[CH2:1]([N:3]([CH2:25][CH3:26])[CH2:4][CH2:5][N:6]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13](=[N:20][NH:21][C:22]([NH2:24])=[S:23])[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]1=2)[CH3:2].[Cl:27][CH2:28][CH:29]=O>CN(C)C=O>[ClH:27].[ClH:27].[S:23]1[CH:29]=[CH:28][N:24]=[C:22]1[NH:21][N:20]=[C:13]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=2[N:6]([CH2:5][CH2:4][N:3]([CH2:1][CH3:2])[CH2:25][CH3:26])[C:7]2[C:12]1=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 14014925HCID 14014925, compound

Product 1

HCID 24832717N,N-Diethyl-2-{9-[2-(1,3-thiazol-2-yl)hydrazinylidene]acridin-10(9H)-yl}ethan-1-amine--hydrogen chloride (1/2)

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6.1 g of 10-[2-(diethylamino)ethyl]-9-acridanone thiosemicarbazone in 100 ml of dimethylformamide is stirred for about 18 hours with 4.3 ml of chloroacetaldehyde (50 percent solution in water). The mixture is subsequently evaporated, the residue is taken up in 50 ml of ethanol, made acid to Congo red with ethanolic hydrochloric acid and the crystals formed are filtered. The crystals are washed successively with ethanol, ether and petroleum ether and there is obtained 10-[2-(diethylamino)ethyl]-9-acridanone (2-thiazolyl)hydrazone dihydrochloride of melting point 214°-216° (decomposition).

Workup

  1. customThe mixture is subsequently evaporated
  2. customthe crystals formed
  3. filtrationare filtered
  4. washThe crystals are washed successively with ethanol, ether and petroleum ether

Sources & evidence

ORD record
ord-4e5702b56cac4d1088b142913a79fbed
Source dataset
uspto-grants-1987_12
Patent number
US04711889

Reaction notes

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