Acetic Acid → HCID 67498017, compound

HRID 74313Notes

Reaction equation

HRID 74313 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=3[N:16]=2)=[CH:8][C:7]=1[N+:21]([O-])=O.[C:24](O)(=O)[CH3:25]>[Fe]>[O:13]1[C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=[C:12]1[C:9]1[CH:10]=[CH:11][C:6]2[N:5]([CH2:4][CH2:3][S:2][CH3:1])[C:24]([CH3:25])=[N:21][C:7]=2[CH:8]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 67498515N-(2-(methylthio)ethyl)-4-(benzoxazol-2-yl)-2-nitroaniline

Product 1

HCID 67498017HCID 67498017, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

To N-(2-(methylthio)ethyl)-4-(benzoxazol-2-yl)-2-nitroaniline (370 mg, 1.12 mmol) was added iron powder (188 mg, 3.37 mmol) and acetic acid (5 mL), and this was heated to reflux for 10 hours. After the reaction solution was cooled, it was concentrated. The residue obtained was purified by silica gel column chromatography to yield the title compound (305 mg, 84% yield) as pink crystals.

Workup

  1. temperaturethis was heated
  2. temperatureto reflux for 10 hours
  3. temperatureAfter the reaction solution was cooled
  4. concentrationit was concentrated
  5. customThe residue obtained
  6. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-08b3d63d714e4b7fbf514d8a143b8fd6
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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