Hydrochloric Acid → HCID 10377841, compound

HRID 487840Notes

Reaction equation

HRID 487840 reaction equation
[CH3:1][S:2]([O:5]S(C)(=O)=O)(=O)=[O:3].[NH2:10][C:11]1[CH:20]=[C:19]([C:21]([O:23]C)=[O:22])[CH:18]=[CH:17][C:12]=1[C:13]([O:15]C)=[O:14].[OH-].[K+].Cl>O>[CH3:1][S:2]([NH:10][C:11]1[CH:20]=[C:19]([C:21]([OH:23])=[O:22])[CH:18]=[CH:17][C:12]=1[C:13]([OH:15])=[O:14])(=[O:5])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 79336Dimethyl aminoterephthalateHCID 81560Methanesulfonic anhydride

Product 1

HCID 10377841HCID 10377841, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
130 °C

Procedure

First, 2-methylsulfonamidoterephthalic acid was prepared as follows. 19.4 g methanesulfonic anhydride was placed in a flask and heated to produce a liquid. 10.3 g dimethyl 2-aminoterephthalate was added to the liquid over a period of 2-3 minutes. The mixture was initially heated at 130° C. for 15 minutes and then at 100° C. for 2 hours and 30 minutes. The mixture was then cooled, 50 ml of cold water added, the mixture stirred for 1 hour and then filtered. The precipitate was recrystallized from 100 ml of methanol which yielded 10 g precipitate having a melting point of 120° C. To a flask were added 1 g of the precipitate, 40 ml of water and 0.6 g potassium hydroxide and the mixture stirred at room temperature. After 15 minutes the slurry became a solution and stirring continued for a total of 12 hours. The solution was then acidified to a pH of about 2 with 6 molar hydrochloric acid to produce a thick precipitate. The precipitate was filtered and dried to yield 0.4 g of a material having a melting point of 296°-298° C. The material was identified by NMR through its potassium salt to be 2-(methylsulfonamido)terephthalic acid.

Workup

  1. temperatureheated
  2. customto produce a liquid
  3. custom30 minutes
  4. temperatureThe mixture was then cooled
  5. filtrationfiltered
  6. customThe precipitate was recrystallized from 100 ml of methanol which
  7. customyielded 10 g
  8. stirringthe mixture stirred at room temperature
  9. waitAfter 15 minutes the slurry became
  10. stirringa solution and stirring
  11. customcontinued for a total of 12 hours
  12. customto produce a thick precipitate
  13. filtrationThe precipitate was filtered
  14. customdried

Sources & evidence

ORD record
ord-6035efac59dd4a53b086095683c95ed4
Source dataset
uspto-grants-1994_03
Patent number
US05298189

Reaction notes

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