Ethyl Acetate → N-(3,4-Dimethyl-5-isoxazolyl)benzo[b]thiophene-2-sulfonamide

HRID 234322

反応式

HRID 234322 の反応式
[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([NH2:8])[O:4][N:3]=1.[S:9]1[C:13]([S:14](Cl)(=[O:16])=[O:15])=[CH:12][C:11]2[CH:18]=[CH:19][CH:20]=[CH:21][C:10]1=2.C(OCC)(=O)C>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([NH:8][S:14]([C:13]2[S:9][C:10]3[CH:21]=[CH:20][CH:19]=[CH:18][C:11]=3[CH:12]=2)(=[O:15])=[O:16])[O:4][N:3]=1

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 883175-Amino-3,4-dimethylisoxazoleHCID 27763331-Benzothiophene-2-sulfonyl chloride

生成物 1

HCID 23445482N-(3,4-Dimethyl-5-isoxazolyl)benzo[b]thiophene-2-sulfonamide収率 60%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒

実験手順

3,4-Dimethyl-5-amino-isoxazole (0.224 g, 2.0 mmol) and 50 mg of DMAP were stirred in 5 ml of pyridine at 25° C. The benzo[b]thiophene-2-sulfonyl chloride (0.16 g, 2.6 mmol) was added and the dark brown-yellow reaction mixture was stirred for 18 h at ambient temperature, poured into 100 ml of ethyl acetate and washed with 2% HCl (3×50 ml). The organic phase was dried with MgSO4, filtered and concentrated to collect 0.61 g of a brown oil/solid. The brown oil/solid was subjected to flash chromatography (30% ethyl acetate/hexanes) to provide 0.37 g of a light brown solid. This was stirred in 10 ml of methanol and 0.5 g of NaOH. The methanolic solution was heated for reflux for 1 h, then cooled to 25° C. and the methanol was removed in vacuo. The resulting residue was acidified to pH 1 with 2% HCl (100 ml) and extracted with ethyl acetate (2×50 ml) The organic phase was dried with MgSO4, filtered and concentrated to collect 0.225 g of a yellow-orange solid. This was recrystallized from CHCl3 /hexanes to produce a light tan-yellow solid (0.194 g, 31% yield), m.p. 157°-160° C.

後処理

  1. washwashed with 2% HCl (3×50 ml)
  2. dry with materialThe organic phase was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto collect 0.61 g of a brown oil/solid

出典と根拠

ORDレコード
ord-8b2ab3543fee4037aba028ebd4df5eff
出典データセット
uspto-grants-1997_01
特許番号
US05594021

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