Sodium Methoxide → HCID 21282824, compound

HRID 1764423Notes

Reaction equation

HRID 1764423 reaction equation
[CH3:1][C:2]1[C:3]([NH:12][S:13]([NH:16][CH:17]([CH3:19])[CH3:18])(=[O:15])=[O:14])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5](OC)=[O:6].C[O-].[Na+]>CO>[CH3:1][C:2]1[C:3]2[NH:12][S:13](=[O:15])(=[O:14])[N:16]([CH:17]([CH3:19])[CH3:18])[C:5](=[O:6])[C:4]=2[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 13609244HCID 13609244, compound

Product 1

HCID 21282824HCID 21282824, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-methyl-2-((((1-methylethyl)amino)-sulfonyl)amino)benzoate (19.9 grams; 0.07 mole) and sodium methylate (7.5 grams; 0.14 mole) were mixed with 200 ml. of methanol and the resulting mixture heated at the reflux temperature thereof for a period of about four hours. The reaction mixture was then cooled and the methanol removed in vacuo. The resulting residue was dissolved in 200 ml. of water and the resulting solution extracted with 100 ml. of ether. The aqueous layer was then separated and acidified to a pH of about 2.0 with concentrated hydrochloric acid. The resulting precipitate formed upon acidification was recovered by filtration, dried and recrystallized from cyclohexane. As a result of these operations, the desired 8-methyl-3-(1-methylethyl)-1H-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide compound was obtained as a crystalline solid having a melting point of 126.5°-127.5° C. and having carbon, hydrogen and nitrogen contents of 51.70, 5.63 and 11.15 percent, respectively, as compared with the theoretical contents of 51.93, 5.51 and 11.02 percent, respectively, calculated for the named structure.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. customthe methanol removed in vacuo
  3. dissolutionThe resulting residue was dissolved in 200 ml
  4. extractionof water and the resulting solution extracted with 100 ml
  5. customThe aqueous layer was then separated
  6. customThe resulting precipitate formed upon acidification
  7. filtrationwas recovered by filtration
  8. customdried
  9. customrecrystallized from cyclohexane
  10. customAs a result of these operations

Sources & evidence

ORD record
ord-e28b6c32a8a146d9b0dedd83f35cf443
Source dataset
uspto-grants-1978_09
Patent number
US04116672

Reaction notes

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