Hydrochloric Acid → HCID 54274117, compound

HRID 654462Notes

Reaction equation

HRID 654462 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH2:12]([O:14][C:15](=[O:25])[C:16]1[C:17](=[C:19]([Cl:24])[CH:20]=[C:21]([Cl:23])[CH:22]=1)[NH2:18])[CH3:13].[ClH:26]>N1C=CC=CC=1.C(OCC)C>[CH2:12]([O:14][C:15](=[O:25])[C:16]1[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[C:17]=1[N:18]([S:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:26])=[CH:3][CH:4]=1)(=[O:10])=[O:9])[S:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9])[CH3:13]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 73984-Chlorobenzenesulfonyl chlorideHCID 15087809HCID 15087809, compound

Product 1

HCID 54274117HCID 54274117, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

138.0 g of 4-chlorobenzenesulfonic acid chloride are added in portions, at room temperature, to a solution of 50.0 g of 3,5-dichloroanthranilic acid ethyl ester in 210 ml of dry pyridine. The reaction mixture is heated to 80°-90° C. and stirred for 28 hours at that temperature to complete the reaction. After cooling, the reaction mixture is poured onto ice/water and acidified with 2N hydrochloric acid. The sticky, oily precipitate is dissolved in diethyl ether, and the aqueous phase is removed. The organic phase is washed with water and saturated sodium chloride solution. After drying over magnesium sulfate, the ether is evaporated off and the crystals remaining are stirred in a mixture of diethyl ether/hexane 4:1. The crystals, which are filtered off, weigh 87.3 g after drying and correspond to the title compound (m.p. 148°-150° C.).

Workup

  1. temperatureThe reaction mixture is heated to 80°-90° C.
  2. customthe reaction
  3. temperatureAfter cooling
  4. additionthe reaction mixture is poured onto ice/water
  5. customthe aqueous phase is removed
  6. washThe organic phase is washed with water and saturated sodium chloride solution
  7. dry with materialAfter drying over magnesium sulfate
  8. customthe ether is evaporated off
  9. stirringthe crystals remaining are stirred in a mixture of diethyl ether/hexane 4:1
  10. filtrationThe crystals, which are filtered off
  11. customafter drying

Sources & evidence

ORD record
ord-cc8476ce6b45428b9f1a3ea411f4750d
Source dataset
uspto-grants-1992_07
Patent number
US05132314

Reaction notes

Loading…