p-Toluenesulfonic acid → Meloxicam

HRID 224607노트

반응식

HRID 224607 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])[N:4]([CH3:14])[C:3]=1[C:15]([NH:17][C:18]1C=CC=CC=1)=[O:16].NC1[S:26][C:27]([CH3:30])=[CH:28][N:29]=1.C1(C)C=CC(S(O)(=O)=O)=CC=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]([NH:17][C:18]1[S:26][C:27]([CH3:30])=[CH:28][N:29]=1)=[O:16]

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 3517702-Amino-5-methylthiazoleHCID 546847802H-1,2-Benzothiazine-3-carboxamide, 4-hydroxy-2-methyl-N-phenyl-, 1,1-dioxide

생성물 1

HCID 54677470Meloxicam수율 24%

시약·촉매·용매 1

HCID 7237O-Xylene용매

실험 절차

1.0 gm (3 millimols) of 4-hydroxy-2-methyl-N-phenyl-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide were refluxed with 1.15 gm (10 millimols) of 2-amino-5-methyl-thiazole and 0.1 gm of p-toluenesulfonic acid in 250 ml of xylene for 72 hours. After cooling, the reaction mixture was washed with 2N hydrochloric acid and with water, dried and evaporated in vacuo. The residue was purified column-chromatographically (Merck-silica gel 60; particle size: 0.2-0.5 mm; eluant: chloroform/ethanol, 95:5), yielding 0.25 gm (24% of theory) of 4-hydroxy-2-methyl-N-(5-methy-2-thiazolyl)-2H-1,2-benzothiazine-3-caboxamide-1,1-dioxide.

후처리

  1. temperatureAfter cooling
  2. washthe reaction mixture was washed with 2N hydrochloric acid and with water
  3. customdried
  4. customevaporated in vacuo
  5. customThe residue was purified column-chromatographically (Merck-silica gel 60; particle size: 0.2-0.5 mm; eluant: chloroform/ethanol, 95:5)

출처 및 근거

ORD 기록
ord-f432adac9e5044f6adb1fdcf037a7279
출처 데이터셋
uspto-grants-1980_11
특허 번호
US04233299

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