2-Mercaptobenzoic Acid → HCID 19887629, compound

HRID 654477Notes

Reaction equation

HRID 654477 reaction equation
C1(S[C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH2:17][CH:18]([N:20]([OH:24])[C:21]([NH2:23])=[O:22])C)[CH:9]=2)C=CC=CC=1.C(O)(=O)C1C(=CC=CC=1)S.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>>[N:10]1([CH2:17][CH2:18][N:20]([OH:24])[C:21]([NH2:23])=[O:22])[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:9]1

Participants

5

Reactant 4

HCID 54432-Mercaptobenzoic AcidHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 19887627HCID 19887627, compound

Product 1

HCID 19887629HCID 19887629, compound

Procedure

A mixture of N-[1-(3-phenylthioindol-1-yl)prop-2-yl]-N-hydroxy urea from Example 3 (100 mg, 0.34 mmol), thiosalicylic acid (208 mg, 1.4 mmol) and trifluoroacetic acid (3 mL) was stirred at r.t. for one hour. The reaction mixture was then poured onto an aqueous saturated NaHCO3 solution and extracted with EtOAc. The combined organic phase was then washed with 1N NaOH, brine, dried and evaporated to dryness. Separation of two products by flash chromatography using 90% EtOAc in hexanes gave the N-[2-(indol-1-yl)eth-1-yl]-N-hydroxy urea, m.p.: 150°-152° C., and the N-[2-(2-phenylthioindole-1-yl)eth-1-yl]-N-hydroxy urea, m.p.: 57°-60° C.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic phase was then washed with 1N NaOH, brine
  3. customdried
  4. customevaporated to dryness
  5. customSeparation of two products by flash chromatography

Sources & evidence

ORD record
ord-e29c161a6a884e2b9384ce0b3be65e71
Source dataset
uspto-grants-1992_07
Patent number
US05132319

Reaction notes

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