Hydrochloric Acid → HCID 21520062, compound

HRID 1282787Notes

Reaction equation

HRID 1282787 reaction equation
N[C:2]1[C:3]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:4]([S:11][CH2:12][CH3:13])[CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].N([O-])=O.[Na+].[ClH:25].[S:26](=[O:28])=[O:27]>[OH-].[Na+].[Cu](Cl)Cl.C(O)(=O)C>[Cl:25][S:26]([C:2]1[C:3]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:4]([S:11][CH2:12][CH3:13])[CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8])(=[O:28])=[O:27]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 21520102HCID 21520102, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 21520062HCID 21520062, compound

Reagents, catalysts & solvents 3

HCID 24014Cupric ChlorideCatalystHCID 176Acetic AcidSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 5-amino-3-ethylthio-4-phenoxybenzoic acid (1.16 g) in 1 N sodium hydroxide (4 ml), sodium nitrite (0.28 g) is added. The solution is added slowly to a mixture of acetic acid (10 ml) and concentrated hydrochloric acid (10 ml) while stirring and keeping the temperature of 2°-5°C. The resulting diazonium mixture is poured into acetic acid (20 ml), saturated with sulphur dioxide and containing copper chloride (0.2 g CuCl2, 2 H2O). The reaction mixture is allowed to reach room temperature while stirring. After cooling, the precipitated 3-ethylthio-5-chlorosulfonyl-4-phenoxybenzoic acid is collected by filtration, washed with aqueous acetic acid, and dried in vacuo at room temperature.

Workup

  1. customthe temperature of 2°-5°C
  2. customto reach room temperature
  3. stirringwhile stirring
  4. temperatureAfter cooling
  5. filtrationthe precipitated 3-ethylthio-5-chlorosulfonyl-4-phenoxybenzoic acid is collected by filtration
  6. washwashed with aqueous acetic acid
  7. customdried in vacuo at room temperature

Sources & evidence

ORD record
ord-2a3cacba1b4d4ecb85c0876838460e31
Source dataset
uspto-grants-1976_08
Patent number
US03972886

Reaction notes

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