2-Thiocresol → HCID 21506012, compound

HRID 918639Notes

Reaction equation

HRID 918639 reaction equation
Cl[C:2]1[C:10]([S:11](=[O:14])(=[O:13])[NH2:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].[CH3:18][C:19]1[C:24]([SH:25])=[CH:23][CH:22]=[CH:21][CH:20]=1>C(=O)(O)[O-].[Na+]>[N+:15]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([S:11](=[O:14])(=[O:13])[NH2:12])[C:2]=1[S:25][C:24]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH3:18])[C:6]([OH:8])=[O:7])([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 87122-ThiocresolHCID 898934-Chloro-3-nitro-5-sulphamoylbenzoic acid

Product 1

HCID 21506012HCID 21506012, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 4-chloro-3-nitro-5-sulphamyl-benzoic acid (28 g), o-thiocresol (12.4 g), and 1N sodium bicarbonate (300 ml) was refluxed for 3 hours. After cooling, the precipitated sodium salt of 3-nitro-5-sulphamyl-4-o-tolylthio-benzoic acid was filtered off and washed with 1N sodium bicarbonate solution. The sodium salt was dissolved in hot water (250 ml), and the acid was precipitated by the addition of 4N hydrochloric acid (17 ml). After isolation, recrystallization from aqueous ethanol, and drying at 115°C and 10 mm Hg for 3 hours, the acid was obtained with a melting point of 165°-166°C.

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperatureAfter cooling
  3. filtrationthe precipitated sodium salt of 3-nitro-5-sulphamyl-4-o-tolylthio-benzoic acid was filtered off
  4. washwashed with 1N sodium bicarbonate solution
  5. dissolutionThe sodium salt was dissolved in hot water (250 ml)
  6. customthe acid was precipitated by the addition of 4N hydrochloric acid (17 ml)
  7. customAfter isolation, recrystallization from aqueous ethanol
  8. customdrying at 115°C
  9. customthe acid was obtained with a melting point of 165°-166°C.

Sources & evidence

ORD record
ord-ffd4b63e727b43e399d041dab136d41c
Source dataset
uspto-grants-1976_07
Patent number
US03971819

Reaction notes

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