Methylamine → 3-(2-bromo-6-chlorophenyl)-N-methylpropanamide

HRID 1471677노트

반응식

HRID 1471677 반응식
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][CH2:10][C:11]([O:13]CC)=O.[C-:16]#[N:17].[Na+].CN>>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][CH2:10][C:11]([NH:17][CH3:16])=[O:13]

참가 물질

4

반응물 3

HCID 6329MethylamineHCID 8929Sodium CyanideHCID 67982372Ethyl 3-(2-bromo-6-chlorophenyl)propanoate

생성물 1

HCID 679825833-(2-bromo-6-chlorophenyl)-N-methylpropanamide

실험 절차

Ethyl 3-(2-bromo-6-chlorophenyl)propanoate (Example 1f), 5.0 g, 17.1 mmol) and sodium cyanide (0.168 g, 3.43 mmol) were stirred in methanamine (8 M in ethanol, 30 mL, 240 mmol) at rt overnight. The solvent was evaporated, the residue was taken up in ethyl acetate and the mixture was washed with saturated aqueous sodium carbonate and brine. The organic phase was separated and the solvent was removed by rotary evaporation. The crude product was added to a silica gel column and was eluted with 0-100% ethyl acetate in heptane. The collected fractions were combined and the solvent was removed by rotary evaporation to give the title product. Yield 2.98 g, 63%. 1H NMR (500 MHz, CDCl3) δ ppm 2.40-2.47 (m, 2H) 2.85 (d, 3H) 3.28-3.35 (m, 2H) 5.44 (br. s., 1H) 7.02 (t, 1H) 7.33 (dd, Hz, 1H) 7.47 (dd, Hz, 1H). MS m/z 277.9 [M+H]+.

후처리

  1. customThe solvent was evaporated
  2. washthe mixture was washed with saturated aqueous sodium carbonate and brine
  3. customThe organic phase was separated
  4. customthe solvent was removed by rotary evaporation
  5. additionThe crude product was added to a silica gel column
  6. washwas eluted with 0-100% ethyl acetate in heptane
  7. customthe solvent was removed by rotary evaporation

출처 및 근거

ORD 기록
ord-7a722d3e224c494fb66e05f61f821503
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012457B2

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