Sulfuric Acid → HCID 58382955, compound

HRID 1629628Notes

Reaction equation

HRID 1629628 reaction equation
[CH2:1]([N:3]([CH2:17][CH3:18])[C:4]([CH:6]1[CH2:15][C:14](=O)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[S:7]1)=[O:5])[CH3:2].Cl.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28]N)=[CH:24][CH:23]=1.S(=O)(=O)(O)O>C(O)C>[CH2:1]([N:3]([CH2:17][CH3:18])[C:4]([CH:6]1[C:15]2[C:26]3[C:25](=[CH:24][CH:23]=[C:22]([O:21][CH3:20])[CH:27]=3)[NH:28][C:14]=2[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[S:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 57852690HCID 57852690, compound

Product 1

HCID 58382955HCID 58382955, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (+−)-4-Oxo-thiochroman-2-carboxylic acid diethyl amide (50) (1.32 g, 5.0 mmol) and 4-methoxyphenyl hydrazine hydrochloride (0.87 g, 5.0 mmol) in ethanol (10 ml) was added concentrated sulphuric acid (0.73 ml, 1.35 g, 13.8 mmol) under nitrogen. The reaction mixture was heated under reflux for 24 h. After cooling, the reaction mixture was filtered, the solid washed with ethanol, dried in vacuo (45° C.) to give the title compound (51) (1.05 g, 57%) as a pale yellow solid. The structure was confirmed by 13C NMR (75 MHz, DMSO-d6) δ 10.5, 12.7, 32.7, 37.9, 39.5, 53.0, 97.6, 103.3, 109.87, 109.92, 120.3, 123.5, 123.8, 124.3, 124.7, 124.9, 127.8, 129.4, 131.8, 151.3, 166.2.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 24 h
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered
  5. washthe solid washed with ethanol
  6. customdried in vacuo (45° C.)

Sources & evidence

ORD record
ord-dc0f55b14ce74a3f9921cc5402df47be
Source dataset
uspto-grants-2014_07
Patent number
US08790619B2

Reaction notes

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