Oxalyl chloride → Ethyl 6,8-dichloro-7-(4-(4-chlorophenethylcarbamoyl)phenoxy)chroman-4-carboxylate

HRID 1021426노트

반응식

HRID 1021426 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:22])[C:11]=1[O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=O)=[CH:15][CH:14]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:23]([O:25][CH2:26][CH3:27])=[O:24].C(Cl)(=O)C(Cl)=O.[Cl:34][C:35]1[CH:40]=[CH:39][C:38]([CH2:41][CH2:42][NH2:43])=[CH:37][CH:36]=1.C(N(C(C)C)CC)(C)C>ClCCl.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:22])[C:11]=1[O:12][C:13]1[CH:14]=[CH:15][C:16]([C:17](=[O:19])[NH:43][CH2:42][CH2:41][C:38]3[CH:39]=[CH:40][C:35]([Cl:34])=[CH:36][CH:37]=3)=[CH:20][CH:21]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:23]([O:25][CH2:26][CH3:27])=[O:24]

참가 물질

7

반응물 4

HCID 65578Oxalyl chlorideHCID 674302-(4-Chlorophenyl)ethylamineHCID 81531DiisopropylethylamineHCID 670803034-(6,8-Dichloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acid

생성물 1

HCID 67080461Ethyl 6,8-dichloro-7-(4-(4-chlorophenethylcarbamoyl)phenoxy)chroman-4-carboxylate수율 98.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

4-(6,8-Dichloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acid (22.96 g, 55.832 mmol) was dissolved in dichloromethane (200 ml) and DMF (0.2 ml). Oxalyl chloride (8.6 ml, 98.585 mmol) was added slowly over a period of 30 minutes at ambient temperature. The crude mixture was concentrated under reduced pressure. Dry dichloromethane (200 ml) was added and the mixture was cooled in an ice bath. 2-(4-Chlorophenyl)ethylamine (8.5413 ml, 61.415 mmol) and diisopropylethylamine (11.701 ml, 66.999 mmol) were added sequentially to the mixture. The mixture was stirred in an ice bath for 10 minutes and warmed to ambient temperature. The crude mixture was washed with 1N HCl (100 ml), water (2×50 ml), and brine (50 ml), dried over MgSO4, filtered through GF paper, and concentrated to provide 30.1 g of a light brown solid after drying under high vacuum for 2 hours. The crude solid was recrystallized from hot EtOAc-hexanes to provide 26.8 g of the title compound as a light brown solid (87%).

후처리

  1. concentrationThe crude mixture was concentrated under reduced pressure
  2. additionDry dichloromethane (200 ml) was added
  3. temperaturethe mixture was cooled in an ice bath
  4. washThe crude mixture was washed with 1N HCl (100 ml), water (2×50 ml), and brine (50 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered through GF paper
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-98af8070bc95400482aabdac6d169202
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716498B2

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