Nitrogen → 3-(2,4-Dichloro-benzylamino)-5-phenyl-thiophene-2-carboxylic acid methyl ester

HRID 2193904

반응식

HRID 2193904 반응식
[H-].[Na+].[CH3:3][O:4][C:5]([C:7]1[S:8][C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:10][C:11]=1[NH2:12])=[O:6].N#N.[Cl:21][C:22]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:23]=1[CH2:29]Cl>CN(C)C=O>[CH3:3][O:4][C:5]([C:7]1[S:8][C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:10][C:11]=1[NH:12][CH2:29][C:23]1[CH:24]=[CH:25][C:26]([Cl:28])=[CH:27][C:22]=1[Cl:21])=[O:6]

참가 물질

6

반응물 4

HCID 947NitrogenHCID 72122,4-Dichlorobenzyl chlorideHCID 24758Sodium hydrideHCID 700562Methyl 3-amino-5-phenylthiophene-2-carboxylate

생성물 1

HCID 207757543-(2,4-Dichloro-benzylamino)-5-phenyl-thiophene-2-carboxylic acid methyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

Sodium hydride (60% dispersion in oil, 180 mg, 4.72 mmol) was added to an ice-cold solution of 3-Amino-5-phenyl-thiophene-2-carboxylic acid methyl ester (1000 mg, 4.29 mmol) in 25 ml of dimethylformamide in an atmosphere of N2. After 5 min, 2,4-dichloro-1-chloromethyl-benzene (755 mg, 3.86 mmol) was added to the solution and then the reaction mixture was stirred for 30 min at 0° C. and 30 min at room temperature. The mixture was partitioned between ether (20 mL) and water (20 mL) and the organic layer was separated. The aqueous phase was washed twice with ether (2×20 mL) and the combined ether layer was dried (MgSO4) and concentrated. The residue obtained was then purified by precipitation. The crude product was taken in 25 ml of ethyl acetate, a yellow precipitate came out which was filtered to obtain 3-(2,4-Dichloro-benzylamino)-5-phenyl-thiophene-2-carboxylic acid methyl ester, 835 mg (55%). 1H-NMR (DMSO, 400 MHz): 7.67 ppm (m, 2H, Haro); 7.44-7.35 ppm (m, 6H, Haro); 7.26 ppm (s, 1H, Haro); 4.63 ppm (d, 2H, N—CH2); 3.75 ppm (s, 3H, O—CH3)

후처리

  1. customThe mixture was partitioned between ether (20 mL) and water (20 mL)
  2. customthe organic layer was separated
  3. washThe aqueous phase was washed twice with ether (2×20 mL)
  4. dry with materialthe combined ether layer was dried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue obtained
  7. customwas then purified by precipitation
  8. filtrationwas filtered

출처 및 근거

ORD 기록
ord-bc95ecdcdc9b46d683cb1be509c2c9d8
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08329924B2

연결된 노트

불러오는 중…