p-Toluenesulfonic acid → HCID 178498595, compound

HRID 1695461Notes

Reaction equation

HRID 1695461 reaction equation
[CH3:1][O:2][C:3](=[O:13])/[C:4](/[N:10](C)[NH2:11])=[CH:5]\[C:6](OC)=[O:7].[C:14]1([CH3:24])[CH:19]=CC(S(O)(=O)=O)=CC=1.[C:25]1([CH3:32])C(C)=CC=C[CH:30]=1>>[CH3:1][O:2][C:3]([C:4]1[CH:5]=[C:6]([OH:7])[N:11]([CH3:14])[N:10]=1)=[O:13].[CH:25]([O:2][CH:14]([CH3:19])[CH3:24])([CH3:32])[CH3:30]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7237O-XyleneHCID 12492956HCID 12492956, compound

Product 2

HCID 7914Diisopropyl EtherHCID 178498595HCID 178498595, compoundYield 74%

Procedure

To a solution of (E)-2-(N-methyl-hydrazino)-but-2-enedioic acid dimethyl ester (12.2 g, 65 mmol) in xylene (65 mL) was added para-toluenesulfonic acid (0.9 g, 4.7 mmol) and the resulting mixture heated at reflux for 6 h. After cooling to room temperature the mixture was stirred overnight and the resulting solid was filtered off and dissolved in ethyl acetate and the organic extract washed with sodium hydrogen carbonate, brine, dried over sodium sulfate, filtered and concentrated to afford the title compound (7.49, 74%) as a light brown solid after trituration with diisopropylether. MS: m/e=157.2 [M+H]+.

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux for 6 h
  3. filtrationthe resulting solid was filtered off
  4. dissolutiondissolved in ethyl acetate
  5. extractionthe organic extract
  6. washwashed with sodium hydrogen carbonate, brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-d8d36c6d04ca4f59a9e08237853d9207
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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