Dicyclohexylcarbodiimide → 4-chloro-N-methoxy-N-methylbenzo[b]thiophene-2-carboxamide

HRID 1773821노트

반응식

HRID 1773821 반응식
[Cl:1][C:2]1[C:10]2[CH:9]=[C:8]([C:11]([OH:13])=O)[S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.Cl.[CH3:15][NH:16][O:17][CH3:18].C1CCC(N=C=NC2CCCCC2)CC1.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:1][C:2]1[C:10]2[CH:9]=[C:8]([C:11]([N:16]([O:17][CH3:18])[CH3:15])=[O:13])[S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 38545164-Chlorobenzo(b)thiophene-2-carboxylic Acid

생성물 1

HCID 224738924-chloro-N-methoxy-N-methylbenzo[b]thiophene-2-carboxamide수율 75.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Stir a mixture of 4-chlorobenzo[b]thiophene-2-carboxylic acid (0.94 g, 4.44 mmol), N,O-dimethylhydroxylamine hydrochloride (0.86 g, 8.87 mmol), DCC (1.1 g, 5.32 mmol) and DIEA (1.43 g, 1.9 mL, 11.08 mmol) in DCM (8 mL) at ambient temperature for 2 hours. Filter the reaction mixture and the filtrate is washed with brine, dried over anhydrous Na2SO4 and concentrated under vacuum. Purify the residue by column chromatography on silica gel eluting with PE:EtOAc (5:1 to 3:1) to afford 4-chloro-N-methoxy-N-methylbenzo[b]thiophene-2-carboxamide as white solid (0.85 g, 75.2%). 1H NMR (400 MHz, CDCl3) δ 8.10-8.02 (m, 2H), 7.61-7.51 (m, 2H), 3.84-3.79 (s, 3H), 3.37-3.35 (s, 3H).

후처리

  1. filtrationFilter the reaction mixture
  2. washthe filtrate is washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under vacuum
  5. customPurify the residue by column chromatography on silica gel eluting with PE

출처 및 근거

ORD 기록
ord-0c5c0135fd2148cb90970f06943d21b3
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09255111B2

반응 노트

불러오는 중…