Acetyl chloride → 3-(Acetylamino-methyl)-phthalic acid dimethyl ester

HRID 906696

반응식

HRID 906696 반응식
C(N(CC)CC)C.Cl.[CH3:9][O:10][C:11](=[O:24])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][NH2:19])[C:13]=1[C:20]([O:22][CH3:23])=[O:21].[C:25](Cl)(=[O:27])[CH3:26]>ClCCl>[CH3:9][O:10][C:11](=[O:24])[C:12]1[C:13](=[C:14]([CH2:18][NH:19][C:25](=[O:27])[CH3:26])[CH:15]=[CH:16][CH:17]=1)[C:20]([O:22][CH3:23])=[O:21]

참가 물질

5

반응물 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 21988538Methyl-3-aminomethyl-2-(methoxycarbonyl)benzoate hydrochloride

생성물 1

HCID 210401323-(Acetylamino-methyl)-phthalic acid dimethyl ester수율 80%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
4 °C

실험 절차

Triethylamine (1.87 g, 18 mmol) was added slowly to a stirred suspension of methyl-3-(aminomethyl)-2-(methoxycarbonyl)benzoate hydrochloride (2.0 g, 8 mmol) in dichloromethane (30 ml). The resulting mixture was cooled in an ice bath to 4° C. Acetyl chloride (0.73 g, 9 mmol) was added dropwise at a rate such that the temperature stayed between 4-7° C. After addition was complete, the mixture was stirred in the ice bath for an additional 30 minutes and then allowed to warm to room temperature and maintained for 2 hours. The reaction mixture was washed with water (2×30 ml), brine (30 ml) and dried. Solvent was removed in vacuo and the product was purified by chromatography (dichloromethane/ethyl acetate 6 to 4) to afford 1.65 g (80%) of the product as an oil: 1H NMR (CDCl3) δ 7.86 (d, J=7.7 Hz, 1H), 7.62 (d, J=7.6 Hz); 7.46 (t, J=7.7 Hz); 6.29 (b, 1H), 4.39 (d, J=6.1 Hz, 2H), 3.93 (s, 3H), 3.90 (s, 3H), 1.96 (s, 3H).

후처리

  1. customstayed between 4-7° C
  2. additionAfter addition
  3. temperatureto warm to room temperature
  4. temperaturemaintained for 2 hours
  5. washThe reaction mixture was washed with water (2×30 ml), brine (30 ml)
  6. customdried
  7. customSolvent was removed in vacuo
  8. customthe product was purified by chromatography (dichloromethane/ethyl acetate 6 to 4)

출처 및 근거

ORD 기록
ord-5360fd7b59af4665ac340e4b08098649
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012997B2

연결된 노트

불러오는 중…