Diethylene Glycol → HCID 14572284, compound

HRID 1593625Notes

Reaction equation

HRID 1593625 reaction equation
C1(N[N:8]=[C:9]2[C:14](=O)[CH2:13][CH2:12][CH2:11][CH2:10]2)C=CC=CC=1.[CH2:16](O)[CH2:17][O:18][CH2:19][CH2:20][OH:21].O.[C:24]1(C)[CH:29]=CC(S(O)(=O)=O)=[CH:26][CH:25]=1>C1(C)C=CC=CC=1>[O:21]1[CH2:20][CH2:19][O:18][C:17]21[CH2:16][CH2:26][C:25]1[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:24]=1[CH2:29]2

Participants

5

Reactant 3

HCID 8117Diethylene GlycolHCID 271464HCID 271464, compoundHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 14572284HCID 14572284, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound was prepared essentially according to published procedures (R. F. Borch et al., J. Org. Chem. 38 (15), 2729 (1973); Nader G. et al., French Patent 2729141 (1996)). A mixture of cyclohexane-2,3-dione monophenylhydrazone (10.1 g, 0.05 mol), diethylene glycol (25 mL) and para-toluene sulfonic acid monohydrate (11.4 g, 0.06 mol) in toluene (500 mL) was heated under nitrogen in an oil bath kept at 135° C. with water removal (Dean-Stark). After heating for 15 hours the mixture was cooled, the toluene was decanted and the tarry residue extracted three times with small portions of toluene. The combined organic phase was washed three times with saturated aqueous sodium bicarbonate, and dried over anhydrous magnesium sulfate. Removal of the solvent provided the crude title compound as a brown oil that partially solidified in vacuo (9.2 g). It was used as such in the next step. MS (ES): [M+H]+ @m/z 230.1

Workup

  1. customThe title compound was prepared essentially
  2. temperaturewas heated under nitrogen in an oil bath
  3. customkept at 135° C. with water removal (Dean-Stark)
  4. temperatureAfter heating for 15 hours the mixture
  5. temperaturewas cooled
  6. customthe toluene was decanted
  7. extractionthe tarry residue extracted three times with small portions of toluene
  8. washThe combined organic phase was washed three times with saturated aqueous sodium bicarbonate
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customRemoval of the solvent

Sources & evidence

ORD record
ord-96423f0de7e245b2a843866524fad2b1
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

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