2-Aminocyclohepta-2,4,6-trien-1-one → HCID 54712695, compound

HRID 1719498Notes

Reaction equation

HRID 1719498 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[C:21](=[O:27])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=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[C:21](=[O:27])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:17]

Participants

4

Reactant 2

HCID 226342-Aminocyclohepta-2,4,6-trien-1-oneHCID 54676532methyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

Product 1

HCID 54712695HCID 54712695, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of methyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide (3.0 g) and 2-amino-2,4,6-cycloheptatrien-1-one (1.6 g) in xylene (100 ml) is refluxed for 8 hours. The reaction mixture is then allowed to stand at room temperature for 15 hours. The crystals that have separated out are collected by filtration, washed with toluene and recrystallized from dimethylformamide to give 4-hydroxy-2-methyl-N-(1-oxo-2,4,6-cycloheptatrien-2-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide (0.68 g), m.p. 259°-261° C.

Workup

  1. customThe crystals that have separated out
  2. filtrationare collected by filtration
  3. washwashed with toluene
  4. customrecrystallized from dimethylformamide

Sources & evidence

ORD record
ord-6d587030859c4f349e159f3888e68b46
Source dataset
uspto-grants-1985_09
Patent number
US04540692

Reaction notes

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