Phenol → HCID 20301865, compound

HRID 1732871Notes

Reaction equation

HRID 1732871 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:6](Cl)=[CH:5][C:3]=1[NH2:4].[C:13]1([OH:19])C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[C:8]([O:19][CH3:13])=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4]

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 231082,5-Dichloro-4-nitroaniline

Product 1

HCID 20301865HCID 20301865, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2,5-dichloro-4-nitroaniline (7.0 g), phenol (3.2 g), potassium carbonate (9.7 g) and dry dimethylformamide (50 ml) is stirred and heated at 100° C. for 7.5 hours. The mixture is then poured into 500 ml of ice water and stirred. The aqueous mixture is extracted with ethyl acetate (5×200 ml), the extracts are dried and evaporated to dryness. The residual oil is stirred with methylene chloride (20 ml), the resulting solid is collected and dried to yield 3.5 g of title product, m.p. 122°-124° C.

Workup

  1. stirringstirred
  2. extractionThe aqueous mixture is extracted with ethyl acetate (5×200 ml)
  3. customthe extracts are dried
  4. customevaporated to dryness
  5. stirringThe residual oil is stirred with methylene chloride (20 ml)
  6. customthe resulting solid is collected
  7. customdried

Sources & evidence

ORD record
ord-ad2cbb9d76134f389849f3383f01adaa
Source dataset
uspto-grants-1980_12
Patent number
US04239708

Reaction notes

Loading…