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

HRID 1979974

반응식

HRID 1979974 반응식
[CH3:1][N:2]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[S:3]1(=[O:5])=[O:4].Cl[CH2:15][C:16]([O:18][CH2:19][CH2:20][O:21][CH3:22])=[O:17].[H-].[Na+]>CS(C)=O>[OH:13][C:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[S:3](=[O:5])(=[O:4])[N:2]([CH3:1])[C:15]=1[C:16]([O:18][CH2:19][CH2:20][O:21][CH3:22])=[O:17]

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 679Dimethyl Sulfoxide용매

실험 절차

To a solution of 3.0 g. (0.015 mole) of N-methylsaccharin and 2.3 g. (0.015 mole) of 2-methoxyethyl chloroacetate in 15 ml. of dimethylsulfoxide at 40° C. was added 810 mg. (0.033 mole) of sodium hydride over a 2 hour period. The resulting reaction mixture was stirred for 2 hours at 40°-50° C. and was then quenched in 5% hydrochloric acid solution. The resulting suspension was extracted with methylene chloride (2×100 ml.) and the organic layers separated, combined and washed with water (50 ml.) and a brine solution (50 ml). The organic layer was dried over magnesium sulfate and concentrated to an oil, 4.1 g. The product was purified by dissolution of the residue in 5 ml. of acetone and addition of the acetone slowly to 125 ml. of 0.25N hydrochloric acid. The suspension was allowed to stir for several hours, and was then filtered and dried 2.6 g. (55%). The product is indistinguishable from that reported in U.S. patent application Ser. No. 191,716, filed Sept. 29, 1980.

후처리

  1. customThe resulting reaction mixture
  2. customwas then quenched in 5% hydrochloric acid solution
  3. extractionThe resulting suspension was extracted with methylene chloride (2×100 ml.)
  4. customthe organic layers separated
  5. washwashed with water (50 ml.)
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated to an oil, 4.1 g
  8. customThe product was purified by dissolution of the residue in 5 ml
  9. additionof acetone and addition of the acetone slowly to 125 ml
  10. stirringto stir for several hours
  11. filtrationwas then filtered
  12. customdried 2.6 g

출처 및 근거

ORD 기록
ord-33ca2cfe254448de8beff2fbeb0ac78c
출처 데이터셋
uspto-grants-1984_11
특허 번호
US04483982

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