Diisopropylethylamine → 2-(pivaloyloxymethyl)-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxide

HRID 1289829

반응식

HRID 1289829 반응식
[CH:1]([C:4]1[C:9]2[C:10](=[O:15])[NH:11][S:12](=[O:14])(=[O:13])[C:8]=2[CH:7]=[C:6]([O:16][CH3:17])[CH:5]=1)([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[C:27]([O:33][CH2:34]Cl)(=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29]>C(#N)C>[C:27]([O:33][CH2:34][N:11]1[C:10](=[O:15])[C:9]2[C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][C:6]([O:16][CH3:17])=[CH:7][C:8]=2[S:12]1(=[O:14])=[O:13])(=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 87885Chloromethyl pivalateHCID 101473624-Isopropyl-6-methoxysaccharin

생성물 1

HCID 110899612-(pivaloyloxymethyl)-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxide수율 91%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a suspension of 4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (1.020 kg, 4.2 mol) in 6 L of acetonitrile was added diisopropylethylamine (543 g, 4.2 mol) and the reaction mixture was stirred at ambient temperature for 30 minutes. At the end of this period, chloromethyl pivalate (633 g, 4.2 mol) was added in one portion and the resulting solution was refluxed on a steam bath for 20 hours. The acetonitrile was removed under vacuum and the residue was stirred with 6 L of water for 30 minutes. The off-white solid was collected by filtration, washed first with 6 L of water, followed by 3 L of hexane. The product was dried at 70° C. under vaccum for 18 hours to give 1.33 kg (91%) of 2-(pivaloyloxymethyl)-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxide, m.p. 178°-179° C.

후처리

  1. temperaturethe resulting solution was refluxed on a steam bath for 20 hours
  2. customThe acetonitrile was removed under vacuum
  3. stirringthe residue was stirred with 6 L of water for 30 minutes
  4. filtrationThe off-white solid was collected by filtration
  5. washwashed first with 6 L of water
  6. customThe product was dried at 70° C. under vaccum for 18 hours

출처 및 근거

ORD 기록
ord-1a1786eb55f5433f8deaba00aa701fc0
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05750550

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