Hydrochloric Acid → HCID 15567167, compound

HRID 1995383Notes

Reaction equation

HRID 1995383 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)N.N([O-])=O.[Na+].[S:17](=[O:19])=[O:18]>C(O)(=O)C.O.[Cu](Cl)Cl.[Cu]Cl>[CH3:2][O:3][C:4]1[CH:5]=[C:6]([S:17]([Cl:1])(=[O:19])=[O:18])[CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 663013,5-DimethoxyanilineHCID 23668193Sodium Nitrite

Product 1

HCID 15567167HCID 15567167, compound

Reagents, catalysts & solvents 4

HCID 24014Cupric ChlorideCatalystHCID 62652Cuprous chlorideCatalystHCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

50 ml of concentrated aqueous hydrochloric acid were added, while cooling (reaction temperature: max. +20° C.) to a solution of 26.6 gm (0.174 mol) of 3,5-dimethoxyaniline in 100 ml of glacial acetic acid. Over a period of 35 minutes a solution of 12 gm (0.174 mol) of sodium nitrite in 25 ml of water was added at -8° to -3° C. while cooling. After stirring for 1 hour on a cold bath, the reaction mixture was filtered, and the dark-brown filtrate was poured at 20°-25° C. into a stirred suspension of 10.2 gm (60 mmols) of copper (II)-chloride and 2 gm (20 mmols) of copper(I)-chloride in 120 ml of a 30% solution of sulfur dioxide in glacial acetic acid. The reaction temperature first rose to 40° C. and after it fell the reaction mixture was heated at 40° C. for another 90 minutes. After partial evaporation, the reaction mixture was poured into 2 liters of ice water. After three extractions with ether, the organic extracts were washed with water, sodium bicarbonate solution and again with water.

Workup

  1. temperaturewhile cooling
  2. temperaturewhile cooling
  3. filtrationthe reaction mixture was filtered
  4. customfirst rose to 40° C.
  5. customAfter partial evaporation
  6. additionthe reaction mixture was poured into 2 liters of ice water
  7. extractionAfter three extractions with ether
  8. washthe organic extracts were washed with water, sodium bicarbonate solution and again with water

Sources & evidence

ORD record
ord-5738769607b84789bb91410abc9fa85e
Source dataset
uspto-grants-1983_09
Patent number
US04404230

Reaction notes

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