Hydrochloric Acid → 5,5-Dioxo-5H-5lambda~6~-thianthrene-3-carboxylic acid

HRID 2398776Notes

Reaction equation

HRID 2398776 reaction equation
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=1Cl)[C:14]([OH:16])=[O:15])(=[O:10])=[O:9].Cl.N([O-])=O.[Na+].O(CC)C([S-])=[S:28].[K+].[OH-].[Na+]>O>[C:14]([C:13]1[CH:17]=[CH:18][C:19]2[S:28][C:2]3[C:3]([S:8](=[O:10])(=[O:9])[C:11]=2[CH:12]=1)=[CH:4][CH:5]=[CH:6][CH:7]=3)([OH:16])=[O:15]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 2735045Potassium ethylxanthateHCID 203841823-(2-Aminobenzene-1-sulfonyl)-4-chlorobenzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 203841685,5-Dioxo-5H-5lambda~6~-thianthrene-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

3-(o-Aminophenylsulphonyl)-4-chlorobenzoic acid (6.00 g) was stirred with concentrated hydrochloric acid (8.0 ml) and water (12.0 ml) and treated at 0°-5° C. with a solution of sodium nitrite (1.50g) in water (30 ml) over 30 min. After a further 15 min. stirring the suspension was pipetted into a solution of potassium ethyl xanthate (10.2g) and sodium hydroxide (1.60g) in water (50 ml) at 45°-50° C. Vigorous nitrogen evolution took place. After the addition was complete the now clear solution was heated to boiling and further sodium hydroxide (3.20g) was added. Boiling was continued for a further 20 min., and the solution then cooled, filtered and acidified with hydrochloric acid. The solid precipitated acid was filtered off, washed with water, and recrystallised from acetic acid to give 3-carboxythianthrene-5,5-dioxide, m.p. 297°-304° C.; on further recrystallisation from ethanol it had m.p. 302°-305° C.

Workup

  1. additionAfter the addition
  2. temperaturewas heated
  3. waitBoiling was continued for a further 20 min.
  4. temperaturethe solution then cooled
  5. filtrationfiltered
  6. customThe solid precipitated acid
  7. filtrationwas filtered off
  8. washwashed with water
  9. customrecrystallised from acetic acid

Sources & evidence

ORD record
ord-b9c515e4c7c7406fa2218d5e2ab3a21b
Source dataset
uspto-grants-1977_05
Patent number
US04025635

Reaction notes

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