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

HRID 1520756ノート

反応式

HRID 1520756 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0d28dd345df04f348f6c09dd33835276
出典データセット
uspto-grants-2015_07
特許番号
US09073920B2

反応ノート

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