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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 2286201
Notes
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Reaction equation

HRID 2286201 reaction equation
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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

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

Product 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

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
170 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4e323eef4d0443309812db31d1290cf3
Source dataset
uspto-grants-1982_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04327091

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes