Water → HCID 54091092, compound

HRID 1719508Notes

Reaction equation

HRID 1719508 reaction equation
[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]1[C:19](=[O:25])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:16].[C:26](Cl)(=[O:35])[CH:27]=[CH:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.N1C=CC=CC=1.O>CN(C)C=O>[O:25]=[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=[C:18]1[NH:17][C:15]([C:3]1[N:4]([CH3:14])[S:5](=[O:12])(=[O:13])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[C:2]=1[O:1][C:26](=[O:35])[CH:27]=[CH:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 660233-Phenylprop-2-enoyl chlorideHCID 54712695HCID 54712695, compound

Product 1

HCID 54091092HCID 54091092, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-hydroxy-2-methyl-N-(1-oxo-2,4,6-cycloheptatrien-2-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide (2.0 g) and cinnamoyl chloride (1.3 g) in N,N-dimethylformamide (30 ml) was added pyridine (0.9 ml). The mixture was stirred at room temperature for 2.5 hours. The reaction mixture was poured into cooled water to give crystals, which were collected by filtration and washed with water. The crude crystals were dissolved in chloroform and the solution was washed successively with water and brine, dried over anhydrous magnesium sulfate, treated with activated charcoal and evaporated under reduced pressure to give crystals. The crystals were recrystallized from a mixture of ethyl acetate and hexane to give N-(1-oxo-2,4,6-cycloheptatrien-2-yl)-2-methyl-4-cinnamoyloxy-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide (2.4 g).

Workup

  1. additionThe reaction mixture was poured
  2. customto give crystals, which
  3. filtrationwere collected by filtration
  4. washwashed with water
  5. dissolutionThe crude crystals were dissolved in chloroform
  6. washthe solution was washed successively with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. additiontreated with activated charcoal
  9. customevaporated under reduced pressure
  10. customto give crystals
  11. customThe crystals were recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-0a0628a938a149ba88ece2f2259f305c
Source dataset
uspto-grants-1985_09
Patent number
US04540692

Reaction notes

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