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Dimethylformamide → 2,5-Dichloro-4-(1,1,2,2-tetrafluoroethoxy)benzenamine

HRID 463452
Notes
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Reaction equation

HRID 463452 reaction equation
CN(C)C=O.Cl.[NH2:7][C:8]1[C:13]([Cl:14])=[CH:12][C:11]([OH:15])=[C:10]([Cl:16])[CH:9]=1.[OH-].[K+].[F:19][C:20]([F:24])=[C:21]([F:23])[F:22]>O>[Cl:14][C:13]1[CH:12]=[C:11]([O:15][C:21]([F:23])([F:22])[CH:20]([F:24])[F:19])[C:10]([Cl:16])=[CH:9][C:8]=1[NH2:7]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8301TetrafluoroethyleneHCID 14797Potassium HydroxideHCID 135172884-Amino-2,5-dichlorophenol hydrochloride

Product 1

HCID 135172892,5-Dichloro-4-(1,1,2,2-tetrafluoroethoxy)benzenamine

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
85 °C

Procedure

A mixture of 100 ml dimethylformamide (DMF), 75 g (0.035 mole) 4-amino-2,5-dichlorophenol, hydrochloride, and 3.0 g (0.05 mole) KOH (pellets ground to powder) was placed in a 500 ml 3-necked round bottom flask fitted with a mechanical stirrer, thermometer and reflux condenser and was stirred for about 1 hour. It was then heated to 85° C. with stirring and 6.0 g (0.06 mole) of tetrafluoroethylene was bubbled in while heating at 85°-90° C. The addition took about 10 minutes. The reactor and contents were cooled in an ice water bath and 200 ml of water were added. The product was extracted with 200 ml methylene chloride and then again with 100 ml methylene chloride. The extracts were combined and the solvents removed by vacuum distillation. A residue (7 g) remained.

Workup

  1. customwas placed in a 500 ml 3-necked round bottom flask
  2. customfitted with a mechanical stirrer
  3. temperaturethermometer and reflux condenser
  4. stirringwith stirring
  5. temperaturewhile heating at 85°-90° C
  6. additionThe addition
  7. waittook about 10 minutes
  8. temperatureThe reactor and contents were cooled in an ice water bath
  9. extractionThe product was extracted with 200 ml methylene chloride
  10. customthe solvents removed by vacuum distillation

Sources & evidence

ORD record
ord-987540b5256b4e5b9ac74ffb1b84ae6a
Source dataset
uspto-grants-1985_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04518804

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes