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

HRID 1734627ノート

反応式

HRID 1734627 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-740a41efd6a440388fc85bc69577fc07
出典データセット
uspto-grants-1996_07
特許番号
US05534533

反応ノート

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