Isopropyl chloroacetate → 1,2-Benzisothiazole-2(3H)-acetic acid, 3-oxo-, 1-methylethyl ester, 1,1-dioxide

HRID 2291650

반응식

HRID 2291650 반응식
OC1C2C=CC=CC=2S(=O)(=O)N(C)C=1C(NC1C=CC=CN=1)=O.[Na].[S:25]1([C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:29](=[O:30])[NH:28]1)(=[O:27])=[O:26].Cl[CH2:38][C:39]([O:41][CH:42]([CH3:44])[CH3:43])=[O:40]>CN(C)C=O>[O:30]=[C:29]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:36]=2[S:25](=[O:26])(=[O:27])[N:28]1[CH2:38][C:39]([O:41][CH:42]([CH3:44])[CH3:43])=[O:40]

참가 물질

5

반응물 3

HCID 7759Isopropyl chloroacetateHCID 24181110Benzosulfinide sodium; Garantose sodiumHCID 54676228Piroxicam

생성물 1

HCID 45196241,2-Benzisothiazole-2(3H)-acetic acid, 3-oxo-, 1-methylethyl ester, 1,1-dioxide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A process for manufacturing 4-hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide, of formula I, ##STR6## which comprises the following reaction sequence: reacting saccharin sodium with isopropyl chloroacetate in dimethylformamide to obtain isopropyl 3-oxo-1,2-benzoisothiazoline-2-acetate 1,1-dioxide, of formula II ##STR7## reacting the isopropyl 3-oxo-1,2-benzoisothiazoline-2-acetate 1,1-dioxide of formula II with sodium isopropylate in isopropanol at a temperature between 60° C. and the boiling point of the solvent, for a time between 15 minutes and 3 hours, to produce an intermediate of formula III ##STR8## methylating the intermediate of formula III in an aqueous-alcoholic basic medium with dimethyl sulfate to produce an intermediate compound of formula IV ##STR9## condensing the intermediate compound of formula IV with 2-aminopyridine in xylene to obtain a final product of formula I.

후처리

  1. customthe following reaction sequence

출처 및 근거

ORD 기록
ord-c01977ea79364183978338fe2a7b83bc
출처 데이터셋
uspto-grants-1989_01
특허 번호
US04797483

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