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

HRID 1281390노트

반응식

HRID 1281390 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 222375188-(Benzoxazol-2-ylsulfanyl)octylamine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-827df001ff2344139f5580614e523315
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06451827B2

반응 노트

불러오는 중…