Pyridine → 2,5-dichloro-N-(2-methyl-benzooxazol-5-yl)-benzenesulfonamide

HRID 970045ノート

反応式

HRID 970045 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[S:9](Cl)(=[O:11])=[O:10].N1C=CC=CC=1.[NH2:19][C:20]1[CH:21]=[CH:22][C:23]2[O:27][C:26]([CH3:28])=[N:25][C:24]=2[CH:29]=1.C([O-])(O)=O.[Na+]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[S:9]([NH:19][C:20]1[CH:21]=[CH:22][C:23]2[O:27][C:26]([CH3:28])=[N:25][C:24]=2[CH:29]=1)(=[O:11])=[O:10]

参加物

6

反応物 4

HCID 1049PyridineHCID 794012,5-Dichlorobenzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 7379202-Methyl-1,3-benzoxazol-5-amine

生成物 1

HCID 253483472,5-dichloro-N-(2-methyl-benzooxazol-5-yl)-benzenesulfonamide収率 63%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2,5-dichlorobenzenesulphonyl chloride (52 mg, 0.21 mmol) in dichloromethane (1.5 mL) was added pyridine (40 μL, 0.5 mmol) and the mixture was stirred under N2 for 5 min, after which time 5-amino-2-methylbenzoxazole (30 mg, 0.20 mmol) was added. The resulting mixture was stirred for 1 h at room temperature, then saturated NaHCO3 solution was added (8 mL) and the mixture was extracted into ethyl acetate (15 mL). The organic phase was washed with brine, dried (Na2SO4), filtered and evaporated to give a residue that was purified using flash chromatography to afford a pale pink solid (45 mg, 63%), single spot at Rf 0.53 (1:1 hexane:ethyl acetate). mp 193.5-193.9° C., HPLC purity 98% (tR 2.27 min in 10% water-acetonitrile). 1H NMR (CDCl3): δ 7.86 (1H, d, J=2.2 Hz), 7.39 (4H, m), 7.12 (1H, dd, J=8.4, 1.8 Hz), 2.58 (3H, s). LCMS: 355.07 (M−). FAB-MS (MH+, C14H10Cl2N2O3S): calcd 356.9867, found 356.9878.

後処理

  1. stirringThe resulting mixture was stirred for 1 h at room temperature
  2. extractionthe mixture was extracted into ethyl acetate (15 mL)
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give a residue that
  8. customwas purified

出典と根拠

ORDレコード
ord-9409435110f74c319e8c1f0a058f0b18
出典データセット
uspto-grants-2007_12
特許番号
US07309715B2

反応ノート

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