2,6-Dichloroaniline → HCID 178482477, compound

HRID 477736Notes

Reaction equation

HRID 477736 reaction equation
C([N:4]1[C:8]([NH:9][CH3:10])=[N:7][C:6]([S:11](Cl)(=[O:13])=[O:12])=[N:5]1)(=O)C.[Cl:15][C:16]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:17]=1[NH2:18]>N1C=CC=CC=1>[Cl:15][C:16]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:17]=1[NH:18][S:11]([C:6]1[N:7]=[C:8]([NH:9][CH3:10])[NH:4][N:5]=1)(=[O:12])=[O:13]

Participants

4

Reactant 2

HCID 118462,6-DichloroanilineHCID 19872309HCID 19872309, compound

Product 1

HCID 178482477HCID 178482477, compoundYield 59.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

The product of stage (b) (4.34 g) was added with stirring to 2,6-dichloroaniline (3.24 g) in pyridine (30 ml), and the mixture was stirred at 50° C. for 18 hours. After removal of the pyridine, the residue was dissolved in sodium hydroxide solution (50 ml) and was extracted with ethyl acetate (50 ml). The aqueous phase was acidified to pH=4-5 with 2N hydrochloric acid, cooled, and the product was filtered off, washed with a little water, and dried to give 3.49 g of the desired product, mp 285°-287° C.

Workup

  1. customAfter removal of the pyridine
  2. dissolutionthe residue was dissolved in sodium hydroxide solution (50 ml)
  3. extractionwas extracted with ethyl acetate (50 ml)
  4. temperaturecooled
  5. filtrationthe product was filtered off
  6. washwashed with a little water
  7. customdried

Sources & evidence

ORD record
ord-b2e4af3282d64e559492a7c064b2b595
Source dataset
uspto-grants-1989_12
Patent number
US04889553

Reaction notes

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