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

HRID 1577905

反応式

HRID 1577905 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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 ].

後処理

  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

出典と根拠

ORDレコード
ord-4cd2a4cea6a24746995a9190624ead31
出典データセット
uspto-grants-1981_09
特許番号
US04289879

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