Methanol → HCID 21317054, compound

HRID 262933Notes

Reaction equation

HRID 262933 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:20])[C:5]([NH:12][S:13]([NH:16][CH:17]([CH3:19])[CH3:18])(=[O:15])=[O:14])=[C:6]([CH:11]=1)[C:7](OC)=[O:8].CO.C[O-].[Na+].C(=O)(O)[O-].[Na+]>C1C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH3:20])[C:5]2[NH:12][S:13](=[O:15])(=[O:14])[N:16]([CH:17]([CH3:19])[CH3:18])[C:7](=[O:8])[C:6]=2[CH:11]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 10942334Sodium MethoxideHCID 21317050HCID 21317050, compound

Product 1

HCID 21317054HCID 21317054, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

Methyl 5-chloro-3-methyl-2-((((1-methylethyl)amino)sulfonyl)amino)benzoate (26.31 grams; 0.08 mole) was mixed with 200 milliliters (ml) of methanol and sodium methoxide (8.84 grams; 0.164 mole) added thereto. The resulting reaction mixture was heated at the reflux temperature thereof for a period of 5 hours. The solvent was then removed in vacuo leaving a solid brown residue which was dissolved in 200 ml. of water. Sodium bicarbonate (20 grams) was added to the aqueous mixture and the resulting oily layer separated from the aqueous layer. The aqueous layer was acidified with dilute hydrochloric acid and the mixture extracted with ether. The ether extract was reduced in volume by evaporation in vacuo to give a light yellow oil which was dissolved in benzene, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to give a light yellow powder. Recrystallization of the powder from methylene chloride and hexane gave the desired 6-chloro-8-methyl-3-(1-methylethyl)-1H-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide product as a white crystalline solid having a melting point of 142°-144° C.

Workup

  1. additionadded
  2. customThe resulting reaction mixture
  3. temperaturewas heated at the reflux temperature
  4. customThe solvent was then removed in vacuo
  5. customleaving a solid brown residue which
  6. dissolutionwas dissolved in 200 ml
  7. customthe resulting oily layer separated from the aqueous layer
  8. extractionthe mixture extracted with ether
  9. extractionThe ether extract
  10. customwas reduced in volume by evaporation in vacuo
  11. customto give a light yellow oil which
  12. dry with materialdried over anhydrous magnesium sulfate
  13. filtrationfiltered
  14. customevaporated in vacuo
  15. customto give a light yellow powder
  16. customRecrystallization of the powder from methylene chloride and hexane

Sources & evidence

ORD record
ord-303e8334090343a99fb2a23cea69ddbe
Source dataset
uspto-grants-1979_05
Patent number
US04155746

Reaction notes

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