3-Amino-5-methylisoxazole → Isoxicam

HRID 1657400ノート

反応式

HRID 1657400 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])[N:4]([CH3:14])[C:3]=1[C:15]([O:17]C)=O.[NH2:19][C:20]1[CH:24]=[C:23]([CH3:25])[O:22][N:21]=1>C1(C)C(C)=CC=CC=1>[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]([CH3:14])[C:3]=1[C:15](=[O:17])[NH:19][C:20]1[CH:24]=[C:23]([CH3:25])[O:22][N:21]=1

参加物

4

反応物 2

HCID 661723-Amino-5-methylisoxazoleHCID 54676532methyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

生成物 1

HCID 54677972Isoxicam

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

反応条件

温度
25 °C

実験手順

To an appropriate flask equipped for reflux and/or distillation, 900 ml xylene, 40 grams (0.149 moles) methyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide and 19.94 grams (0.203 moles) of 3-amino-5-methylisoxazole are added. The mixture is refluxed for 13-18 hours. At 1 hour intervals, about 3-4% of the solvent volume is distilled off. Every 4 to 5 hours fresh xylene is added, equal in amount to that distilled during this period. At the end of the heating period, the reaction is cooled to 25°C., filtered and the cake is washed with xylene. After drying, the crude product weighed 43.8 grams (88%). This material could be recrystallized from about 40-50 volumes of dioxane with an 80-85% recovery of acceptable material. An alternate procedure for the purification of crude product is as follows:

後処理

  1. customTo an appropriate flask equipped
  2. temperaturefor reflux
  3. additionare added
  4. temperatureThe mixture is refluxed for 13-18 hours
  5. distillationAt 1 hour intervals, about 3-4% of the solvent volume is distilled off
  6. additionEvery 4 to 5 hours fresh xylene is added, equal in amount to
  7. distillationthat distilled during this period
  8. filtrationfiltered
  9. washthe cake is washed with xylene
  10. customAfter drying
  11. customThis material could be recrystallized from about 40-50 volumes of dioxane with an 80-85% recovery of acceptable material
  12. customAn alternate procedure for the purification of crude product

出典と根拠

ORDレコード
ord-7f8f94b999314c13b4f06989a21f3ff7
出典データセット
uspto-grants-1976_06
特許番号
US03960856

反応ノート

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