2-Mercaptobenzoic Acid → HCID 19426235, compound

HRID 742527Notes

Reaction equation

HRID 742527 reaction equation
I[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7](I)[CH:8]=2)[CH:3]=1.[C:13]([OH:22])(=[O:21])[C:14]1[C:15](=[CH:17][CH:18]=[CH:19][CH:20]=1)[SH:16].[C:23](=[O:26])([O-])[O-:24].[K+].[K+].CN(C)C=O>O>[C:13]([C:14]1[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=1[S:16][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:16][C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[C:23]([OH:24])=[O:26])[CH:8]=2)[CH:3]=1)([OH:22])=[O:21]

Participants

6

Reactant 4

HCID 54432-Mercaptobenzoic AcidHCID 6228Dimethylformamide2×HCID 11430Potassium CarbonateHCID 1189482,6-Diiodonaphthalene

Product 1

HCID 19426235HCID 19426235, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2,6-diiodonaphthalene (38.0 grams, 0.10 mole), thiosalicyclic acid (30.8 grams, 0.20 mole), potassium carbonate (27.3 grams, 0.20 mole) and N,N-dimethylformamide (200 ml) was heated and stirred at 130°-135° C. for 8 hours. An isolated sample showed mostly starting material and half-reacted product. More N,N-dimethylformamide (50.0 ml) was added and the reaction mixture was heated for an additional 30 hours at about 150° C. The reaction mixture was drowned into water (500 ml) and the "milky" mixture was filtered using Celite filter aid to remove the unreacted 2,6-diiodonaphthalene. The filtrate was acidified with concentrated HCl to precipitate the product which was collected by filtration and washed with water. The wet cake was ground using a mortar and pestle and then reslurried in methanol. After collecting the solid by filtration, washing with methanol and drying in air, forty grams of crude product were obtained.

Workup

  1. temperaturewas heated
  2. customhalf-reacted product
  3. filtrationthe "milky" mixture was filtered
  4. filtrationfilter aid
  5. customto remove the unreacted 2,6-diiodonaphthalene
  6. customto precipitate the product which
  7. filtrationwas collected by filtration
  8. washwashed with water
  9. customAfter collecting the solid
  10. filtrationby filtration
  11. washwashing with methanol
  12. customdrying in air

Sources & evidence

ORD record
ord-06b6528cdce74581a4d2ce66a719ef05
Source dataset
uspto-grants-1996_09
Patent number
US05554720

Reaction notes

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