Dimethylamine → N,N-Dimethyl-3-(7-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)propan-1-amine

HRID 424543노트

반응식

HRID 424543 반응식
Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][S:8][C:7]2[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:6]1=2.[CH3:18][NH:19][CH3:20].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[CH3:18][N:19]([CH3:20])[CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][S:8][C:7]2[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:6]1=2

참가 물질

7

반응물 4

HCID 674DimethylamineHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 591440694-(3-Chloropropyl)-7-nitro-3,4-dihydro-2H-benzo[b][1,4]thiazine

생성물 1

HCID 59144154N,N-Dimethyl-3-(7-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)propan-1-amine수율 42%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

A solution of 4-(3-chloropropyl)-7-nitro-3,4-dihydro-2H-benzo[b][1,4]thiazine (0.7 g, 2.57 mmol), dimethylamine (2M solution in THF) (2.57 mL, 5.13 mmol), potassium iodide (0.426 g, 2.57 mmol), and potassium carbonate (1.773 g, 12.83 mmol) in dry acetonitrile (20 mL) was stirred at 80° C. for 6 hours in a sealed tube. The reaction was then brought to room temperature and diluted with water (60 mL), and the product was extracted into ethyl acetate (3×20 mL). The combined ethyl acetate layers were washed with brine (20 mL) and dried (Na2SO4). The solvent was evaporated, and the crude material was purified by column chromatography (1:9 (2 M NH3 in MeOH):CH2Cl2) on silica gel to obtain the title product (0.3 g, 42%) as a thick syrup. 1H NMR (DMSO-d6) δ 7.85-7.80 (m, 2H), 6.85 (d, 1H, J=8.7 Hz), 3.77 (t, 2H, J=5.1 Hz), 3.47 (t, 2H, J=7.2 Hz), 3.06 (t, 2H, J=5.1 Hz), 2.24 (t, 2H, J=6.6 Hz), 2.14 (s, 6H), 1.75-1.65 (m, 2H); ESI-MS (m/z, %): 282 (MH+, 100).

후처리

  1. customwas then brought to room temperature
  2. extractionthe product was extracted into ethyl acetate (3×20 mL)
  3. washThe combined ethyl acetate layers were washed with brine (20 mL)
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was evaporated
  6. customthe crude material was purified by column chromatography (1:9 (2 M NH3 in MeOH):CH2Cl2) on silica gel

출처 및 근거

ORD 기록
ord-52b36dd77957493e8dfeaa4038306082
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106043B2

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