Sulfuric Acid → HCID 57852687, compound

HRID 1890150Notes

Reaction equation

HRID 1890150 reaction equation
[C:1]1([N:7]([CH2:9][CH2:10][OH:11])N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:12]([N:14]([CH2:28][CH3:29])[C:15]([CH:17]1[CH2:26][C:25](=O)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[S:18]1)=[O:16])[CH3:13].S(=O)(=O)(O)O>C(O)C>[CH2:28]([N:14]([CH2:12][CH3:13])[C:15]([CH:17]1[C:26]2[C:6]3[C:1](=[CH:2][CH:3]=[CH:4][CH:5]=3)[N:7]([CH2:9][CH2:10][OH:11])[C:25]=2[C:24]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[S:18]1)=[O:16])[CH3:29]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 39491Ethanol, 2-(1-phenylhydrazino)-HCID 57852690HCID 57852690, compound

Product 1

HCID 57852687HCID 57852687, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(N-phenyl-hydrazino)-ethanol (ii) (0.59 g, 1.9 mmol) and 4-oxo-thiochroman-2-carboxylic acid diethylamide (iii) (0.5 g, 1.9 mmol) in ethanol 10 ml was added conc. sulfuric acid 0.5 ml. The reaction mixture was stirred and refluxed for 20 hours. It was then cooled to room temperature and poured onto water 50 ml. The resulting precipitate was collected by filtration and washed with water (3×30 ml). It was then dried in desiccators under vacuum with P2O5 as the drying agent to give the product 11-(2-Hydroxy-ethyl)-6,11-dihydro-5-thia-11-aza-benzo[α]fluorene-6-carboxylic acid diethylamide (iv) as a yellow solid 0.62 g, which was used to next step without further purification. Yield: 86%.

Workup

  1. temperaturerefluxed for 20 hours
  2. additionpoured onto water 50 ml
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with water (3×30 ml)
  5. dry with materialIt was then dried in desiccators under vacuum with P2O5 as the drying agent

Sources & evidence

ORD record
ord-b625dbae06664e4c826f7ae1ed6ff6e0
Source dataset
uspto-grants-2013_08
Patent number
US08506932B2

Reaction notes

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