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7-Amino-4-methylcoumarin → 2-methyl-3,4-dihydro-4-oxo-N-(2-oxo-4-methyl-2H-1-benzopyran-7-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide

HRID 2057888
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HRID 2057888 반응식
CO[C:3]([CH:5]1[C:10](=[O:11])[C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[S:7](=[O:17])(=[O:16])[N:6]1[CH3:18])=[O:4].[CH3:19][C:20]1[C:29]2[C:24](=[CH:25][C:26]([NH2:30])=[CH:27][CH:28]=2)[O:23][C:22](=[O:31])[CH:21]=1>C1(C)C(C)=CC=CC=1>[CH3:18][N:6]1[CH:5]([C:3]([NH:30][C:26]2[CH:27]=[CH:28][C:29]3[C:20]([CH3:19])=[CH:21][C:22](=[O:31])[O:23][C:24]=3[CH:25]=2)=[O:4])[C:10](=[O:11])[C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[S:7]1(=[O:16])=[O:17]
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참가 물질

4

반응물 2

HCID 922497-Amino-4-methylcoumarinHCID 120152Methyl 3,4-dihydro-2-methyl-4-oxo-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

생성물 1

HCID 132906052-methyl-3,4-dihydro-4-oxo-N-(2-oxo-4-methyl-2H-1-benzopyran-7-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide

시약·촉매·용매 1

HCID 7237O-Xylene용매

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온도
170 °C

실험 절차

8.1 g of 2-methyl-3,4-dihydro-4-oxo-2H-1,2-benzothiazine-3-carboxylic acid methyl ester 1,1-dioxide and 5.7 g of 4-methyl-7-amino-coumarin are dissolved in 280 ml of xylene and the solution is heated for 21/2 hours in a bath of 170° C. to distill off the methanol formed during the reaction. The reaction mixture is refluxed for a further 5 hours, cooled, and the precipitate is collected by filtration. The precipitate is digested with 100 ml of 2N-hydrochloric acid at elevated temperature, treated with 100 ml of chloroform and extracted. The residue is collected by suction, washed successively with water, ethanol, methylene chloride and diethyl ether, washed, and dried, affording 2-methyl-3,4-dihydro-4-oxo-N-(2-oxo-4-methyl-2H-1-benzopyran-7-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide with a melting point above 285° C.

후처리

  1. distillationto distill off the methanol
  2. customformed during the reaction
  3. temperatureThe reaction mixture is refluxed for a further 5 hours
  4. temperaturecooled
  5. filtrationthe precipitate is collected by filtration
  6. additiontreated with 100 ml of chloroform
  7. extractionextracted
  8. customThe residue is collected by suction
  9. washwashed successively with water, ethanol, methylene chloride and diethyl ether
  10. washwashed
  11. customdried

출처 및 근거

ORD 기록
ord-749bf7db5a154a30a095a0bb11e46ad8
출처 데이터셋
uspto-grants-1980_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04213980

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