Dichloromethane → SPA-S 510; Sinartol; Sinartrol; Zelis; Zen

HRID 745658Notes

Reaction equation

HRID 745658 reaction equation
[C:1]([O:11][C:12]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[S:15](=[O:23])(=[O:22])[N:14]([CH3:24])[C:13]=1[C:25]([OH:27])=O)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(Cl)Cl.[NH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=1>C(OCC)C>[C:1]([O:11][C:12]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[S:15](=[O:23])(=[O:22])[N:14]([CH3:24])[C:13]=1[C:25]([NH:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=1)=[O:27])(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 104392-AminopyridineHCID 53730199HCID 53730199, compound

Product 1

HCID 68605SPA-S 510; Sinartol; Sinartrol; Zelis; Zen

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The cinnamoyl anhydride and the other mixed anhydrides of 4-cinnamoyloxy-2-methyl-2H-1,2-benzothiazine-3-carboxylic acid 1,1-dioxide prepared respectively according to Example 12 or Example 13 are directly reacted, without previous purification or recovery from their methylene chloride solution, with 2-2.5 molar equivalents of 2-aminopyridine with stirring and external cooling. After dilution with 3 volumes of diethyl ether the reaction mixture is stirred at 15° C. for 3 hours, then the procedure of Example 16 is repeated obtaining the desired 4-cinnamoyloxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide.

Workup

  1. customprepared respectively

Sources & evidence

ORD record
ord-4422054b2a6d438da9578e98f150b61e
Source dataset
uspto-grants-1986_07
Patent number
US04599406

Reaction notes

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