Hydrochloric Acid → HCID 13560012, compound

HRID 463961Notes

Reaction equation

HRID 463961 reaction equation
[ClH:1].[Cl:2][C:3]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:4]=1[O:5][C:6]1[CH:7]=[CH:8][C:9](N)=[C:10]([CH:16]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12].Cl.N([O-])=O.[Na+].[S:31](=[O:33])=[O:32]>O.[Cu](Cl)Cl.C(O)(=O)C.C1C=CC=CC=1>[Cl:2][C:3]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:4]=1[O:5][C:6]1[CH:7]=[CH:8][C:9]([S:31]([Cl:1])(=[O:33])=[O:32])=[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:16]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 20249654Ethyl 5-(2-chloro-4-trifluoromethylphenoxy)-2-aminobenzoate hydrochlorideHCID 23668193Sodium Nitrite

Product 1

HCID 13560012HCID 13560012, compound

Reagents, catalysts & solvents 4

HCID 24014Cupric ChlorideCatalystHCID 176Acetic AcidSolvent2×HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

Ethyl 5-(2-chloro-4-trifluoromethylphenoxy)-2-aminobenzoate hydrochloride (12 g) and conc. hydrochloric acid (6.6 ml) were added to acetic acid (85 ml), and the resultant mixture was cooled to less than 10° C. A solution of sodium nitrite (2.5 g) in water (6 ml) was dropwise added thereto. When the resulting mixture became completely transparent, benzene (20 ml), acetic acid (20 ml) saturated with sulfur dioxide and copper chloride (1.5 g) were added thereto. After stirring overnight, the reaction mixture was poured onto ice-water. The deposited oily substance was extracted with chloroform, washed with water and dried over anhydrous magnesium sulfate. The extract was concentrated and allowed to stand. The crystallized substance was recrystallized from hexane to give 9 g of 4-(2-chloro-4-trifluoromethylphenoxy)-2-ethoxycarbonylbenzenesulfonyl chloride. M.P., 96°-96.5° C.

Workup

  1. additionthe reaction mixture was poured onto ice-water
  2. extractionThe deposited oily substance was extracted with chloroform
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe extract was concentrated
  6. customThe crystallized substance was recrystallized from hexane

Sources & evidence

ORD record
ord-1cfd7b754f5947f3b90760328921deeb
Source dataset
uspto-grants-1985_10
Patent number
US04545812

Reaction notes

Loading…