Sulfuric Acid → HCID 10256217, compound

HRID 1592986Notes

Reaction equation

HRID 1592986 reaction equation
COCCOC[O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([N:22]([CH2:24][C:25]3[CH:26]=[C:27]([C:31]4[CH:36]=[CH:35][C:34]([CH2:37][CH:38]5[S:42][C:41](=[O:43])[NH:40][C:39]5=[O:44])=[CH:33][CH:32]=4)[CH:28]=[CH:29][CH:30]=3)[CH3:23])=[O:21])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1.S(=O)(=O)(O)O>CO>[OH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([N:22]([CH2:24][C:25]3[CH:26]=[C:27]([C:31]4[CH:36]=[CH:35][C:34]([CH2:37][CH:38]5[S:42][C:41](=[O:43])[NH:40][C:39]5=[O:44])=[CH:33][CH:32]=4)[CH:28]=[CH:29][CH:30]=3)[CH3:23])=[O:21])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 10348770HCID 10348770, compound

Product 1

HCID 10256217HCID 10256217, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.6 g of 4′-(2-methoxyethoxymethoxy)-N-[4′-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methylbiphenyl-4-carboxamide, 100 ml of methanol and 1 ml of 98% sulphuric acid are introduced, in order, into a 250 ml three-necked flask. The mixture is stirred at room temperature for 18 hours. The reaction medium is concentrated. It is taken up in ethyl acetate and it is washed twice with water. The organic phase is dried over magnesium sulphate. After filtration and evaporation, the product obtained is recrystallized from an acetone/dichloromethane mixture. After filtration and drying, 1.34 g (99%) of 4′-hydroxy-N-[4′-(2,4-dioxothiazolidin-5-ylmethyl )biphenyl-3-ylmethyl]-N-methylbiphenyl-4-carboxamide are obtained in the form of a white powder having a melting point of 211-213° C.

Workup

  1. concentrationThe reaction medium is concentrated
  2. washit is washed twice with water
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. filtrationAfter filtration and evaporation
  5. customthe product obtained
  6. customis recrystallized from an acetone/dichloromethane mixture
  7. filtrationAfter filtration
  8. customdrying

Sources & evidence

ORD record
ord-1ab99246f641447db21c64a0c2d05df4
Source dataset
uspto-grants-2007_11
Patent number
US07294639B2

Reaction notes

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