Triethylamine → Methyl 2-[(3-Bromopropylimino)methyl]phenylcarbamate

HRID 1520756노트

반응식

HRID 1520756 반응식
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10](=[O:13])[O:11][CH3:12])=O.S([O-])([O-])(=O)=O.[Mg+2].Cl.[Br:21][CH2:22][CH2:23][CH2:24][NH2:25].C(N(CC)CC)C>C(Cl)(Cl)Cl>[Br:21][CH2:22][CH2:23][CH2:24][N:25]=[CH:1][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10](=[O:13])[O:11][CH3:12]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 128607653-Bromopropan-1-amine--hydrogen chloride (1/1)HCID 45122974Methyl (2-formylphenyl)carbamate

생성물 1

HCID 49856372Methyl 2-[(3-Bromopropylimino)methyl]phenylcarbamate수율 94.5%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

Methyl 2-formylphenylcarbamate (7, 2.5 g, 14 mmol) and magnesium sulfate (5 g) were added to a solution of 3-bromopropylamine hydrochloride (3.68 g, 16.8 mmol) and triethylamine in chloroform (30 mL) and mixture was stirred for 24 h. The mixture was filtered and the residue was washed with chloroform (2×30 mL). The combined filtrates were washed with water (2×30 mL), brine (30 mL), dried with sodium sulfate, and concentrated to afford 21 as a yellow oil (3.95 g, 94.5%). IR (film) 1730, 1638 cm−1; 1H NMR (300 MHz, CDCl3) δ 8.38 (d, J=8.4 Hz, 1 H), 8.30 (s, 1 H), 7.35 (t, J=7.7 Hz, 2 H), 7.26 (d, J=7.7 Hz, 1 H), 7.00 (t, J=7.4 Hz, 1 H), 3.74 (s, 3 H), 3.69 (t, J=6.3 Hz, 2 H), 3.50 (t, J=6.6 Hz, 2 H), 2.20 (pent, J=6.3 Hz, 2 H); 13C NMR (75 MHz, CDCl3) δ 164.74, 154.30, 140.07, 133.00, 131.32, 121.25, 119.79, 117.69, 58.17, 52.87, 33.16, 31.15; ESIMS m/z (rel intensity) 299/301 (MH+, 100/99); EIHRMS m/z M+ calcd. for C12H15BrN2O2, 298.0317; found, 298.0320.

후처리

  1. filtrationThe mixture was filtered
  2. washthe residue was washed with chloroform (2×30 mL)
  3. washThe combined filtrates were washed with water (2×30 mL), brine (30 mL)
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-0d28dd345df04f348f6c09dd33835276
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073920B2

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