Potassium Hydroxide → HCID 18319545, compound

HRID 1699380Notes

Reaction equation

HRID 1699380 reaction equation
N[C:2]1[C:3]([O:13][CH2:14][CH2:15][CH2:16][C:17]([O:19]CC)=[O:18])=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7]CC)=[O:6].N([O-])=O.[Na+].CCOC([S-])=[S:30].[K+].[OH-].[K+]>Cl.O.C(O)C>[SH:30][C:2]1[C:3]([O:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([OH:7])=[O:6]

Participants

8

Reactant 4

HCID 14797Potassium HydroxideHCID 2735045Potassium ethylxanthateHCID 18319600HCID 18319600, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 18319545HCID 18319545, compoundYield 91.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent2×HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of ethyl 3-amino-2-(3-ethoxycarbonyl-propoxy)benzoate (8.93 g) in conc. hydrochloric acid (4.8 ml) was cooled in an ice bath. To this solution was added dropwise a solution of sodium nitrite (2.11 g) in water (5 ml) at 5° C. On the other hand, a solution of potassium xanthogenate (5.83 g) in water (7.6 ml) was heated at 50° C. To this solution was added dropwise the above solution of the diazonium salt at 50-55° C. The reaction mixture was cooled to room temperature and was extracted with ethyl acetate. After an additional extraction with ethyl acetate, the combined extracts were dried over magnesium sulfate and evaporated in vacuo to give the crude material, which was then dissolved in ethanol and 85% potassium hydroxide (9.10 g) was added to the solution. After the mixture was heated to reflux for 1.5 hours, it was cooled in an ice bath and acidified with conc. hydrochloric acid. The mixture was then extracted with ethyl acetate (x 3). The combined extracts were dried over magnesium sulfate and evaporated in vacuo to give 3-mercapto-2-(3-carboxypropoxy)benzoic acid (7.08 g) as yellow crystals.

Workup

  1. extractionwas extracted with ethyl acetate
  2. extractionAfter an additional extraction with ethyl acetate
  3. dry with materialthe combined extracts were dried over magnesium sulfate
  4. customevaporated in vacuo
  5. customto give the crude material, which
  6. temperatureAfter the mixture was heated
  7. temperatureto reflux for 1.5 hours
  8. temperatureit was cooled in an ice bath
  9. extractionThe mixture was then extracted with ethyl acetate (x 3)
  10. dry with materialThe combined extracts were dried over magnesium sulfate
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-17419378c718425da53fec4c6dce1aff
Source dataset
uspto-grants-2002_02
Patent number
US06346527B1

Reaction notes

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