Potassium Carbonate → 8-(Benzoxazol-2-ylsulfanyl)octylamine

HRID 1743440ノート

反応式

HRID 1743440 の反応式
[SH:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]1C(=O)C2=CC=CC=C2C1=O>CN(C=O)C>[O:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[S:1][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH2:26]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 253681N-(8-Bromooctyl)phthalimideHCID 1784182821,3-benzoxazole-2-thiol

生成物 1

HCID 222375188-(Benzoxazol-2-ylsulfanyl)octylamine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a round bottom flask with 2-mercaptobenzoxazole (2.14 g, 14.2 mmol) and DMF (100 mL) at room temperature was added K2CO3 (2.61 g, 18.9 mmol) followed by N-(8-bromooctyl)phthalimide (4.00 g, 11.8 mmol). The resulting solution was heated to 60° C. for 0.5 h and then cooled back to room temperature. At this point, the reaction mixture was quenched with H2O (100 mL) and then diluted with EtOAc (600 mL). The organic layer was washed with 1 N HCl (60 mL), sat. aq. NaHCO3 (60 mL), and brine (60 mL) and then dried (MgSO4). After concentration, the residue was purified by the Biotage Flash 40 apparatus (10 to 20% EtOAc/petroleum ether gradient) to afford the thioether intermediate.

後処理

  1. temperaturecooled back to room temperature
  2. customAt this point, the reaction mixture was quenched with H2O (100 mL)
  3. additiondiluted with EtOAc (600 mL)
  4. washThe organic layer was washed with 1 N HCl (60 mL), sat. aq. NaHCO3 (60 mL), and brine (60 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationAfter concentration
  7. customthe residue was purified by the Biotage Flash 40 apparatus (10 to 20% EtOAc/petroleum ether gradient)

出典と根拠

ORDレコード
ord-27f580cf016848f8abca7bdd59b30a26
出典データセット
uspto-grants-2006_03
特許番号
US07008636B2

反応ノート

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