Methyl iodide → 6-Methyl-2-(methylsulfanyl)-1,3-benzoxazole

HRID 9579

반응식

HRID 9579 반응식
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]2[NH:6][C:7](=[S:9])[O:8][C:4]=2[CH:3]=1.IC.[C:14](=O)([O-])[O-].[K+].[K+]>C1COCC1>[CH3:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([S:9][CH3:14])[O:8][C:4]=2[CH:3]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 9635016-Methyl-1,3-benzoxazole-2-thiol

생성물 1

HCID 219857886-Methyl-2-(methylsulfanyl)-1,3-benzoxazole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

6-Methyl-1,3-benzoxazole-2(3H)-thione (375 mg, 2.27 mmol) was dissolved in THF (2.0 mL), and iodomethane (1610.8 mg, 11.35 mmol) and potassium carbonate (627.36 mg, 4.54 mmol) were added. This reaction mixture was stirred vigorously at rt overnight. The reaction mixture was filtered and the solid was rinsed with additional THF. The filtrate was concentrated in vacuo to a yellow solid. The solid was partitioned between ethyl acetate and water. The organic layer was separated and washed with brine, dried with MgSO4, and concentrated. The solid was dried for 1 h in a 50° C. oven. The product 6-methyl-2-(methylsulfanyl)-1,3-benzoxazole was obtained as yellow solid (145 mg, 35.6%). 1H NMR (300 MHz, DMSO-d6) δ 7.50 (d, 1 H), 7.20 (s, 1 H), 7.10 (d, 1 H), 2.78 (s, 3 H), 2.42 (s, 3 H); LC-MS ret. time 2.90 min (method 2), m/z 180.1 (MH+).

후처리

  1. filtrationThe reaction mixture was filtered
  2. washthe solid was rinsed with additional THF
  3. concentrationThe filtrate was concentrated in vacuo to a yellow solid
  4. customThe solid was partitioned between ethyl acetate and water
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried with MgSO4
  8. concentrationconcentrated
  9. customThe solid was dried for 1 h in a 50° C. oven

출처 및 근거

ORD 기록
ord-3262dfcd76f846518796ae0f5231d23d
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091228B2

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