Formaldehyde → 2-(Chloromethyl)-4-isopropyl-6-methoxybenzo[D]isothiazol-3(2H)-one 1,1-dioxide

HRID 266460

반응식

HRID 266460 반응식
[CH2:1]=[O:2].Cl[Si](C)(C)C.[Sn](Cl)(Cl)(Cl)[Cl:9].[CH:13]([C:16]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[C:23]2[C:17]=1[C:18](=O)[NH:19][S:20]2(=[O:22])=[O:21])([CH3:15])[CH3:14]>ClCCCl.O>[Cl:9][CH2:18][N:19]1[C:1](=[O:2])[C:17]2[C:23](=[CH:24][C:25]([O:27][CH3:28])=[CH:26][C:16]=2[CH:13]([CH3:15])[CH3:14])[S:20]1(=[O:22])=[O:21]

참가 물질

7

반응물 4

HCID 712FormaldehydeHCID 6397ChlorotrimethylsilaneHCID 24287Tin tetrachlorideHCID 101473624-Isopropyl-6-methoxysaccharin

생성물 1

HCID 99951732-(Chloromethyl)-4-isopropyl-6-methoxybenzo[D]isothiazol-3(2H)-one 1,1-dioxide수율 87%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 962Water용매

실험 절차

To a suspension of 24 g of paraformaldehyde (0.8 mole) and 86.4 g of chlorotrimethylsilane (1.6 moles) in 200 mL of 1,2-dichloroethane was added 0.8 ml anhydrous tin(IV) chloride and the resulting solution stirred on a steam bath for one hour. 4-Isopropyl-6-methoxysaccharin (51.4 g, 0.2 mole) was added to the clear solution and the mixture was refluxed for 18 hours, cooled to room temperature and poured into water. The organic layer was separated, washed with 50 mL of 2N sodium hydroxide solution, dried over anhydrous magnesium sulfate and concentrated under vacuum. The residue was purified by crystallization from ethyl acetate/hexane to give 57 g (87%) of 2-chloromethyl-4-isopropyl-6-methoxysaccharin, mp 151°.

후처리

  1. temperaturethe mixture was refluxed for 18 hours
  2. customThe organic layer was separated
  3. washwashed with 50 mL of 2N sodium hydroxide solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by crystallization from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-a4a4d2119f1540299fbf11e8e6e35785
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05650422

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