2,6-Dichloroaniline → HCID 19872287, compound

HRID 477728Notes

Reaction equation

HRID 477728 reaction equation
[CH2:1]([C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:6]=[C:5]([S:14](Cl)(=[O:16])=[O:15])[N:4]=1)[CH3:2].[Cl:18][C:19]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:20]=1[NH2:21]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[Cl:18][C:19]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:20]=1[NH:21][S:14]([C:5]1[N:4]=[C:3]([CH2:1][CH3:2])[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:6]=1)(=[O:16])=[O:15]

Participants

5

Reactant 2

HCID 118462,6-DichloroanilineHCID 19872291HCID 19872291, compound

Product 1

HCID 19872287HCID 19872287, compoundYield 30.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

5-Ethyl-1-phenyl-1,2,4-triazole-3-sulphonyl chloride (2.7 g), prepared by a method analogous to that of Example A, was added to a stirred solution of 2,6-dichloroaniline (1.8 g), and 4-dimethylaminopyridine (0.1 g) in dry pyridine (15 ml). After 48 hours at 25° C. most of the pyridine was removed in vacuo, and the residue was dissolved in dichloromethane. The solution was extracted with dilute hydrochloric acid and then re-evaporated. The residue was treated with 4M sodium hydroxide solution (25 ml) at 80° C. for 1 hour and then filtered. The filtered solid was washed with warm water, the filtrate was acidified with concentrated hydrochloric acid, and the product was recrystallised from ethanol to give 1.2 g of desired product, mp 185°-187° C.

Workup

  1. customAfter 48 hours at 25° C. most of the pyridine was removed in vacuo
  2. dissolutionthe residue was dissolved in dichloromethane
  3. extractionThe solution was extracted with dilute hydrochloric acid
  4. customre-evaporated
  5. additionThe residue was treated with 4M sodium hydroxide solution (25 ml) at 80° C. for 1 hour
  6. filtrationfiltered
  7. washThe filtered solid was washed with warm water
  8. customthe product was recrystallised from ethanol

Sources & evidence

ORD record
ord-0db4d68abc48418c82b4373d1b1c0841
Source dataset
uspto-grants-1989_12
Patent number
US04889553

Reaction notes

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