3-Methyl-2-butanone → HCID 86600552, compound

HRID 2218531Notes

Reaction equation

HRID 2218531 reaction equation
[CH3:1][CH:2]([CH3:6])[C:3](=O)[CH3:4].[NH:7]([C:9]1[CH:14]=[C:13]([S:15]([OH:18])(=[O:17])=[O:16])[CH:12]=[CH:11][C:10]=1[S:19]([OH:22])(=[O:21])=[O:20])N.C([O-])(=O)C.[K+:27]>C(O)(=O)C>[CH3:4][C:3]1[C:2]([CH3:6])([CH3:1])[C:14]2[C:13]([S:15]([O-:18])(=[O:17])=[O:16])=[CH:12][CH:11]=[C:10]([S:19]([O-:22])(=[O:21])=[O:20])[C:9]=2[N:7]=1.[K+:27].[K+:27]

Participants

5

Reactant 3

HCID 112513-Methyl-2-butanoneHCID 517044Potassium AcetateHCID 13007424HCID 13007424, compound

Product 1

HCID 86600552HCID 86600552, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a three-necked flask equipped with mechanical stirrer and a reflux condenser were added 50 ml of acetic acid, 15 ml (140 mmol) of 3-methyl-2-butanone, 16.2 g (60 mmol) of 2-hydrazino-1,4-benzenedisulfonic acid and 13 g (133 mmol) of potassium acetate. The mixture was heated to reflux for 8 h and then cooled to room temperature. The brownish precipitate was filtered off and washed with acetic acid and acetonitrile. Yield: 13.8 g (58%) of the raw product (1k). 1H-NMR (200 MHz, DMSO-d6), δ, ppm: 7.67 (1H, arom., d, 8.1 Hz), 7.59 (1H, arom., d, 8.2 Hz), 2.44 (3H, CH3, s), 1.57 (6H, (CH3)2, s).

Workup

  1. customTo a three-necked flask equipped with mechanical stirrer and a reflux condenser
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 8 h
  4. filtrationThe brownish precipitate was filtered off
  5. washwashed with acetic acid and acetonitrile

Sources & evidence

ORD record
ord-421ac94f04f44cfbafeb30e63bafb649
Source dataset
uspto-grants-2008_08
Patent number
US07411068B2

Reaction notes

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