2,4,6-Cycloheptatrien-1-one, 5-amino-2-methoxy- → HCID 54712693, compound

HRID 1719503Notes

Reaction equation

HRID 1719503 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]([O:17]C)=O.[NH2:19][C:20]1[CH:26]=[CH:25][C:24](=[O:27])[C:23]([O:28][CH3:29])=[CH:22][CH: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]([NH:19][C:20]1[CH:26]=[CH:25][C:24](=[O:27])[C:23]([O:28][CH3:29])=[CH:22][CH:21]=1)=[O:17]

Participants

4

Reactant 2

HCID 1354432,4,6-Cycloheptatrien-1-one, 5-amino-2-methoxy-HCID 54676532methyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

Product 1

HCID 54712693HCID 54712693, compoundYield 5.2%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

In a nitrogen atmosphere, a solution of methyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide (4.0 g) and 5-amino-2-methoxy-2,4,6-cycloheptatrien-1-one (2.7 g) in xylene (100 ml) is refluxed for 6 hours. The reaction mixture is then allowed to stand at room temperature overnight. The crystals that have separated out are collected by filtration and purified by silica gel (40 g) column chromatography using methanol-dichloromethane (5:95) as the eluent. The resulting crude product is recrystallized from dioxane-methanol to give 4-hydroxy-2-methyl-N-(2-methoxy-1-oxo-2,4,6-cycloheptatrien-5-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide (0.3 g), m.p. 215°-218° C.

Workup

  1. customThe crystals that have separated out
  2. filtrationare collected by filtration
  3. custompurified by silica gel (40 g) column chromatography
  4. customThe resulting crude product is recrystallized from dioxane-methanol

Sources & evidence

ORD record
ord-0921337016b949b9b10a9bc00cf23581
Source dataset
uspto-grants-1985_09
Patent number
US04540692

Reaction notes

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