Hydrochloric Acid → Methyl 2-chloro-6-(chlorosulfonyl)benzoate

HRID 1995396Notes

Reaction equation

HRID 1995396 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6](N)[C:7]=1[C:8]([O:10][CH3:11])=[O:9].[ClH:13].N([O-])=O.[Na+].[S:18](=[O:20])=[O:19]>O.C(O)(=O)C.[Cu]Cl.[Cu](Cl)Cl>[Cl:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([S:18]([Cl:13])(=[O:20])=[O:19])[CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 592849Methyl 2-amino-6-chlorobenzoateHCID 23668193Sodium Nitrite

Product 1

HCID 20488465Methyl 2-chloro-6-(chlorosulfonyl)benzoate

Reagents, catalysts & solvents 4

HCID 24014Cupric ChlorideCatalystHCID 62652Cuprous chlorideCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

34.6 gm (0.186 mol) of methyl 6-chloro-anthranilate were added to 70 ml of concentrated aqueous hydrochloric acid while stirring and cooling. At 0° to +10° C. the reaction mixture was diazotized with a solution of 12.8 gm (0.186 mol) of sodium nitrite in 30 ml of water. After stirring at 0° C. for 45 minutes, the reaction mixture was poured into a stirred suspension of 2 gm of copper(I) chloride and 17 gm of copper (II)chloride in 160 ml of a 30% solution of sulfur dioxide in glacial acetic acid. After the evolution of nitrogen had ceased, the reaction mixture was stirred for 2 hours at room temperature. After extraction with ether, the organic extracts were washed, dried and evaporated.

Workup

  1. temperaturecooling
  2. customAt 0° to +10° C.
  3. stirringAfter stirring at 0° C. for 45 minutes
  4. stirringthe reaction mixture was stirred for 2 hours at room temperature
  5. extractionAfter extraction with ether
  6. washthe organic extracts were washed
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-09a8c36ed600444bbedb7845635002fe
Source dataset
uspto-grants-1983_09
Patent number
US04404230

Reaction notes

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