Acetic Acid → HCID 66584010, compound

HRID 576478Notes

Reaction equation

HRID 576478 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]([O:22][CH:23]([F:25])[F:24])[CH:17]=2)=[CH:10][C:9]=1[CH3:26])([O-])=O>O.C(O)C.[Fe]>[F:25][CH:23]([F:24])[O:22][C:18]1[CH:17]=[C:16]([S:15][C:11]2[CH:10]=[C:9]([CH3:26])[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 66583977HCID 66583977, compound

Product 1

HCID 66584010HCID 66584010, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

7.7 ml of glacial acetic acid (0.135 moles) are added to a solution of 30 g of 2-nitro-5-(3-difluoromethoxyphenylthio)-p-xylene (0.092 moles) in H2O (40 ml) and ethanol (400 ml); 34.7 g of Fe in powder form (0.621 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. When the reaction is completed (GC and TLC analyses), the mixture is cooled to room temperature; the solid is filtered on a celite bed. The ethanol is concentrated at reduced pressure. The crude product obtained is washed with a saturated solution of sodium bicarbonate and extracted with ethyl acetate.

Workup

  1. customis brought to 90° C.
  2. stirringunder stirring for 1.5 hours
  3. temperaturethe mixture is cooled to room temperature
  4. filtrationthe solid is filtered on a celite bed
  5. concentrationThe ethanol is concentrated at reduced pressure

Sources & evidence

ORD record
ord-de4f52406f1841e2bd2bcb353273031d
Source dataset
uspto-grants-2015_05
Patent number
US09040457B2

Reaction notes

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