Phenol → HCID 20301880, compound

HRID 2164040Notes

Reaction equation

HRID 2164040 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])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:6]([O:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:5][C:3]=1[NH2:4]

Participants

5

Reactant 3

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

Product 1

HCID 20301880HCID 20301880, compoundYield 39.1%

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-27ff6a0e595d44e18a7c7594939b3ef4
Source dataset
uspto-grants-1979_01
Patent number
US04137310

Reaction notes

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