Dimethyl Sulfoxide → HCID 178483779, compound

HRID 637583Notes

Reaction equation

HRID 637583 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:35][CH2:36]OS(C3C=CC(C)=CC=3)(=O)=O)[N:7]=[C:8]3[C:17]4[C:12](=[C:13]([O:26]CC5C=CC=CC=5)[CH:14]=[CH:15][C:16]=4[O:18]CC4C=CC=CC=4)[C:11](=[O:34])[C:10]=1[C:9]=23.[CH3:48][N:49]([CH3:53])[CH2:50][CH2:51][NH2:52].[C:54](=[O:57])([O-])[O-].[K+].[K+].CS(C)=O>O>[CH3:48][N:49]([CH3:53])[CH2:50][CH2:51][NH:52][CH2:36][CH2:35][N:6]1[C:5]2[CH:4]=[CH:3][C:2]([NH:52][CH2:51][CH2:50][NH:49][CH2:48][CH2:54][OH:57])=[C:10]3[C:11](=[O:34])[C:12]4[C:17]([C:8]([C:9]=23)=[N:7]1)=[C:16]([OH:18])[CH:15]=[CH:14][C:13]=4[OH:26]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 66053N,N-DimethylethylenediamineHCID 13558467HCID 13558467, compound

Product 1

HCID 178483779HCID 178483779, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4.2 g (6.3 mmol) of 5-chloro-2-[2-[[(4-methylphenyl)sulfonyl]oxy]ethyl]-7,10-bis(phenylmethoxy)anthra[1,9-cd]pyrazol-6(2H)-one, 5.3 g (60 mmol) of N,N-dimethylethylenediamine, 17 g (12.6 mmol) of powdered potassium carbonate, and 35 ml of dimethylsulfoxide is stirred overnight at 50° C. The mixture is cooled and diluted with 50 ml of water. The solid is collected and washed with water. The solid is heated in dichloromethane, the solution filtered, then concentrated. Trituration of the residue with hot ethyl acetate gives 1.7 g of the dried product; mp 148°-153° C.

Workup

  1. temperatureThe mixture is cooled
  2. customThe solid is collected
  3. washwashed with water
  4. temperatureThe solid is heated in dichloromethane
  5. filtrationthe solution filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1d0c148b71484264a7593d471b5039f5
Source dataset
uspto-grants-1985_12
Patent number
US04556654

Reaction notes

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