Sodium hydride → 2-Methoxyethyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

HRID 354637

반응식

HRID 354637 반응식
[H-].[Na+].[CH3:3][N:4]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[S:5]1(=[O:7])=[O:6].Cl[CH2:17][C:18]([O:20][CH2:21][CH2:22][O:23][CH3:24])=[O:19]>CN(C)C=O>[OH:15][C:14]1[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[S:5](=[O:7])(=[O:6])[N:4]([CH3:3])[C:17]=1[C:18]([O:20][CH2:21][CH2:22][O:23][CH3:24])=[O:19]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 272902-methyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxideHCID 2214302-Methoxyethyl Chloroacetate

생성물 1

HCID 546793412-Methoxyethyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

In a manner similar to Example 1B, 1.0 g. of 91% sodium hydride was added over a period of one hour to a solution of 3.0 g. (0.015 mole) of N-methylsaccharin and 2.6 g. (0.017 mole) of 2-methoxyethyl chloroacetate in 15 ml. of dimethylformamide at 35° C. The exothermic reaction (55° C.) was allowed to stir for 2 hours after the addition was complete, and was then quenched in 5% hydrochloric acid solution and the product extracted with methylene chloride. The residue, remaining after the solvent was removed, was dissolved in 10 ml. of warm dimethylformamide and added to 100 ml. of 2% hydrochloric acid. The cooled suspension was stirred for 30 minutes and filtered. Drying of the filtered material gave 1.12 g. (24%) of the product identical with that prepared in Example 1B.

후처리

  1. customat 35° C
  2. customThe exothermic reaction (55° C.)
  3. additionafter the addition
  4. customwas then quenched in 5% hydrochloric acid solution
  5. extractionthe product extracted with methylene chloride
  6. customwas removed
  7. dissolutionwas dissolved in 10 ml
  8. additionof warm dimethylformamide and added to 100 ml
  9. stirringThe cooled suspension was stirred for 30 minutes
  10. filtrationfiltered
  11. customDrying of the filtered material
  12. customgave 1.12 g

출처 및 근거

ORD 기록
ord-a0e7cb77fbfc477d8ebc89be33690d10
출처 데이터셋
uspto-grants-1983_03
특허 번호
US04376204

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