Dimethyl Sulfoxide → HCID 19090645, compound

HRID 1591421Notes

Reaction equation

HRID 1591421 reaction equation
[CH2:1]([S:13][C:14]1[CH:31]=[CH:30][C:29]2[C:28](=[O:32])[C:27]3[C:18](=[C:19](Cl)[C:20]4[C:25]([C:26]=3Cl)=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:17](=[O:35])[C:16]=2[CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[C:36]1([OH:42])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.[C:43](=[O:46])([O-])[O-].[K+].[K+].CS(C)=O>C1(C)C=CC=CC=1>[CH2:1]([S:13][C:14]1[CH:31]=[CH:30][C:29]2[C:28](=[O:32])[C:27]3[C:18](=[C:19]([O:46][C:43]4[CH:5]=[CH:4][CH:3]=[CH:2][CH:1]=4)[C:20]4[C:25]([C:26]=3[O:42][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:17](=[O:35])[C:16]=2[CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 996PhenolHCID 11430Potassium CarbonateHCID 19090643HCID 19090643, compound

Product 1

HCID 19090645HCID 19090645, compoundYield 106.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.20 g (0.38 mmol) of 2-n-dodecylthio-6,11-dichloronaphthacene-5,12-dione, 0.09 g (0.95 mmol) of phenol, 0.21 g (1.52 mmol) of potassium carbonate and 2 ml of DMSO are stirred for 75 minutes at 60° C. The mixture is taken up in toluene and extracted twice with toluene. The toluene phases are washed twice with water, dried over sodium sulfate and concentrated by evaporation. Recrystallisation from ether/pentane gives 0.13 g (54%) of the title compound A, m.p. 165°-8° C.; MS: 642 (M+ ; base peak).

Workup

  1. extractionextracted twice with toluene
  2. washThe toluene phases are washed twice with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated by evaporation
  5. customRecrystallisation from ether/pentane

Sources & evidence

ORD record
ord-baa0225cf00045eb98659e85b32a8e02
Source dataset
uspto-grants-1993_04
Patent number
US05206395

Reaction notes

Loading…