Methyl iodide → 2-Methoxyethyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

HRID 1577905노트

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HRID 1577905 반응식
[OH:1][C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5](=[O:13])(=[O:12])[NH:4][C:3]=1[C:14]([O:16][CH2:17][CH2:18][O:19][CH3:20])=[O:15].[CH3:21]I.[OH-].[Na+]>CC(C)=O>[OH:1][C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5](=[O:12])(=[O:13])[N:4]([CH3:21])[C:3]=1[C:14]([O:16][CH2:17][CH2:18][O:19][CH3:20])=[O:15]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 704814632-Methoxyethyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

생성물 1

HCID 546793412-Methoxyethyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide수율 90.2%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

2-Methoxyethyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide (31.0 g., 0.1035 mole) was combined with 230 ml. of acetone and cooled to 10° C. Methyl iodide (21.9 g., 0.155 mole) was added, followed by the dropwise addition, over 10 minutes, of sodium hydroxide (103.5 ml. of 1 N). The cooling bath was removed and the reaction mixture allowed to slowly warm to room temperature (about 45 minutes), then heated at 35° C. for 2 hours and finally at 39°-40° C. for 16 hours. The reaction mixture was cooled to room temperature, diluted with 200 ml. of acetone, treated with activated carbon, filtered and concentrated in vacuo at 0°-5° C. to about 50 ml. The resulting slurry was filtered, and solids washed with ice-water and then dried in vacuo to yield 2-methoxyethyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide [29.26 g., 90%; m.p. 106°-107.5° C.; m/e 313; ir(KBr) 3345, 2941, 1684, 1351, 1053 cm-1 ].

후처리

  1. customThe cooling bath was removed
  2. temperatureheated at 35° C. for 2 hours and finally at 39°-40° C. for 16 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. additiondiluted with 200 ml
  5. additionof acetone, treated with activated carbon
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo at 0°-5° C. to about 50 ml
  8. filtrationThe resulting slurry was filtered
  9. washsolids washed with ice-water
  10. customdried in vacuo

출처 및 근거

ORD 기록
ord-4cd2a4cea6a24746995a9190624ead31
출처 데이터셋
uspto-grants-1981_09
특허 번호
US04289879

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