5-chloro-2-(chloromethyl)-1H-1,3-benzodiazole → Ethyl n-[(5-chloro-2-benzimidazolyl)methyl]-n-(4-chlorophenyl)glycinate

HRID 1402832

반응식

HRID 1402832 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[Cl:15][C:16]1[CH:26]=[CH:25][C:19]2[N:20]=[C:21]([CH2:23]Cl)[NH:22][C:18]=2[CH:17]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[Cl:15][C:16]1[CH:26]=[CH:25][C:19]2[N:20]=[C:21]([CH2:23][N:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[NH:22][C:18]=2[CH:17]=1

참가 물질

5

반응물 3

HCID 2712865-chloro-2-(chloromethyl)-1H-1,3-benzodiazoleHCID 302644Glycine, N-(4-chlorophenyl)-, ethyl esterHCID 516892Sodium Bicarbonate2회

생성물 1

HCID 66759582Ethyl n-[(5-chloro-2-benzimidazolyl)methyl]-n-(4-chlorophenyl)glycinate수율 22.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
150 °C

실험 절차

The mixture of ethyl N-(4-chlorophenyl)glycinate (0.43 g), 5-chloro-2-chloromethylbenzimidazole (0.4 g), and sodium bicarbonate (0.17 g) in N,N-dimethylformamide (2 ml) was stirred at 150° C. for 0.5 h. After cooling to rt the mixture was poured into saturated sodium bicarbonate solution (50 ml) and extracted twice with EtOAc (40 ml). The combined organic layers were washed with 10% sodium carbonate solution (40 ml) and water (40 ml) and dried (sodium sulfate). After concentration the crude (0.66 g) was purified by flash chromatography (dichloromethane/1% methanol) on silica gel to provide an orange solid. The solid was further purified by trituration with diethyl ether to give ethyl N-[(5-chloro-2-benzimidazolyl)methyl]-N-(4-chlorophenyl)glycinate (0.17 g) as a light orange crystals.

후처리

  1. temperatureAfter cooling to rt the mixture
  2. extractionextracted twice with EtOAc (40 ml)
  3. washThe combined organic layers were washed with 10% sodium carbonate solution (40 ml) and water (40 ml)
  4. dry with materialdried (sodium sulfate)
  5. concentrationAfter concentration the crude (0.66 g)
  6. customwas purified by flash chromatography (dichloromethane/1% methanol) on silica gel
  7. customto provide an orange solid
  8. customThe solid was further purified by trituration with diethyl ether

출처 및 근거

ORD 기록
ord-9831c1577fc64d46b7bb4e74cd716567
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08912186B2

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