Sulfuric Acid → HCID 66712989, compound

HRID 523673Notes

Reaction equation

HRID 523673 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([S:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:8][CH:9]=2)[C:4](=[O:18])[N:3]1[CH2:19][C:20]([OH:22])=[O:21].S(=O)(=O)(O)O.[C:28](=O)(O)[O-].[Na+]>CO>[CH3:28][O:21][C:20](=[O:22])[CH2:19][N:3]1[C:4](=[O:18])[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([S:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:6]=2)[C:2]1=[O:1]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 59645281HCID 59645281, compound

Product 1

HCID 66712989HCID 66712989, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 20 ml of methanol, 6.27 g of (1,3-dioxo-5-phenylsulfanyl-1,3-dihydro-isoindol-2-yl)-acetic acid (20 mmol) and 0.3 ml of concentrated sulfuric acid was refluxed with stirring for 18 h. Then 100 ml of concentrated aqueous sodium bicarbonate solution were added and the mixture was extracted with 100 ml of ethyl acetate. The organic phase was dried over MgSO4 and evaporated in vacuo. 6.30 g of the title compound were obtained; MS-(+)-ion: M+1=328.0; 1H NMR (CDCl3): δ=7.69 (d, 1H), 7.41 to 7.55 (m, 7H), 4.40 (s, 2H), 3.75 (s, 3H).

Workup

  1. temperaturewas refluxed
  2. extractionthe mixture was extracted with 100 ml of ethyl acetate
  3. dry with materialThe organic phase was dried over MgSO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-17258181384f4c64a141cdcfba6a14f9
Source dataset
uspto-grants-2016_05
Patent number
US09339527B2

Reaction notes

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