Triethylamine → 1,1-Dihydroxy-3-oxo-3H-benzo[d]isothiazole

HRID 1734627노트

반응식

HRID 1734627 반응식
Cl.BrCCC[NH2:6].C(N(CC)CC)C.Cl[S:15]([C:18]1[CH:27]=[CH:26][CH:25]=[CH:24][C:19]=1[C:20](OC)=[O:21])(=[O:17])=[O:16]>ClCCl>[OH:16][S:15]1([OH:17])[C:18]2[CH:27]=[CH:26][CH:25]=[CH:24][C:19]=2[C:20](=[O:21])[NH:6]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 117830Benzoic acid, 2-(chlorosulfonyl)-, methyl esterHCID 128607653-Bromopropan-1-amine--hydrogen chloride (1/1)

생성물 1

HCID 152067201,1-Dihydroxy-3-oxo-3H-benzo[d]isothiazole수율 33.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

3-Bromopropylamine hydrochloride (2.189 g, 10 mmol) was suspended in 15 ml of dry dichloromethane, and to the suspension were added triethylamine (7 ml, 50 mmol) and methyl 2(chlorosulfonyl)benzoate (2.738 g, 10.5 mmol). The mixture was stirred at room temperature for 66 hours, poured into ice water, extracted with dichloromethane, washed with water, dried over sodium sulfate, and concentrated. The residue was purified by flash chromatography on silica gel to give 617 mg of 1,1-Dihydroxy-3-oxo-3H-benzo[d]isothiazole (20%). The isothiazole was etherified with Deg. B-Bh-Ester by the NaH/DMF method described above, and the compound was subjected to deprotection to remove the Bh group by the TFA/Anisole method described above, providing 309 mg of the desired compound 120 (97%).

후처리

  1. extractionextracted with dichloromethane
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-740a41efd6a440388fc85bc69577fc07
출처 데이터셋
uspto-grants-1996_07
특허 번호
US05534533

반응 노트

불러오는 중…