Acetic Acid → 4-(3-Hydroxyphenylthio)-2,5-xylidine

HRID 576481Notes

Reaction equation

HRID 576481 reaction equation
C(O)(=O)C.[N+:5]([C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([S:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=2)=[CH:10][C:9]=1[CH3:23])([O-])=O>C(O)C.O.[Fe]>[OH:22][C:18]1[CH:17]=[C:16]([S:15][C:11]2[CH:10]=[C:9]([CH3:23])[C:8](=[CH:13][C:12]=2[CH3:14])[NH2:5])[CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 665838602-Nitro-5-(3-hydroxyphenylthio)-p-xylene

Product 1

HCID 866878084-(3-Hydroxyphenylthio)-2,5-xylidine

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

6.3 ml of glacial acetic acid (0.11 moles) are added to a solution of 20 g of the product obtained in Example 4 (0.076 moles) in 328 ml of ethanol and 33 ml of H2O; 29.7 g of Fe in powder form (0.53 moles) are carefully added to the reaction mixture kept under stirring at 60° C. The temperature is brought to 90° C. and the mixture is kept under stirring for 1.5 hours.

Workup

  1. customis brought to 90° C.
  2. stirringunder stirring for 1.5 hours

Sources & evidence

ORD record
ord-c01d0464b83c46f4bf79b918a41a0202
Source dataset
uspto-grants-2015_05
Patent number
US09040457B2

Reaction notes

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