2-Amino-6-methyl-2,4,6-cycloheptatrien-1-one → 4-hydroxy-2-methyl-N-(6-methyl-1-oxo-2,4,6-cycloheptatrien-2-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide

HRID 1719501Notes

Reaction equation

HRID 1719501 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:28])[CH:22]=[C:23]([CH3:27])[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:28])[CH:22]=[C:23]([CH3:27])[CH:24]=[CH:25][CH:26]=1)=[O:17]

Participants

4

Reactant 2

HCID 125382072-Amino-6-methyl-2,4,6-cycloheptatrien-1-oneHCID 54676532methyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

Product 1

HCID 547126964-hydroxy-2-methyl-N-(6-methyl-1-oxo-2,4,6-cycloheptatrien-2-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxideYield 48.2%

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 (1.2 g) and 2-amino-6-methyl-2,4,6-cycloheptatrien-1-one (0.7 g) in xylene (21 ml) is refluxed for 8 hours. The reaction mixture is then allowed to stand at room temperature for 2 days. The crystals that have separated out are collected by filtration, washed with toluene and recrystallized from dimethylformamide to give 4-hydroxy-2-methyl-N-(6-methyl-1-oxo-2,4,6-cycloheptatrien-2-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide (0.8 g), m.p. 276°-280° 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-0e33d0dc91da4cc7b46bad5b6b17f638
Source dataset
uspto-grants-1985_09
Patent number
US04540692

Reaction notes

Loading…