2-Aminothiophenol → HCID 13285741, compound

HRID 2393175Notes

Reaction equation

HRID 2393175 reaction equation
[C:1]([O:11]CC)(=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O-])=O.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[SH:21]>O>[S:21]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:7]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([OH:11])=[O:10]

Participants

4

Reactant 2

HCID 87132-AminothiophenolHCID 7330447HCID 7330447, compound

Product 1

HCID 13285741HCID 13285741, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of monoethyl heptanedioate (9.41 g), o-aminothiophenol (5.35 ml) and polyphosphoric acid (150 g) was heated to 130° C. with stirring and the reaction was conducted at the same temperature for 2 hours. After cooling to 40° C., pure water (300 ml) was added and the mixture was stirred at 50° C. for 30 minutes. After cooling to room temperature, the reaction mixture was extracted with ethyl acetate (500 ml). The organic layer was extracted with 1N NaOH, acidified with concentrated HCl, and reextracted with ethyl acetate. The extract was dried and concentrated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate) to provide the title compound (4.6 g).

Workup

  1. temperatureAfter cooling to 40° C.
  2. stirringthe mixture was stirred at 50° C. for 30 minutes
  3. temperatureAfter cooling to room temperature
  4. extractionthe reaction mixture was extracted with ethyl acetate (500 ml)
  5. extractionThe organic layer was extracted with 1N NaOH
  6. customThe extract was dried
  7. concentrationconcentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-252f894b36d74c4b808a3ac6c2ba5afb
Source dataset
uspto-grants-1998_09
Patent number
US05804601

Reaction notes

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