Sodium chloroacetate → 5-Chloro-2-(chloromethyl)-1-[3-(methylsulfonyl)propyl]-1H-benzimidazole

HRID 1500843노트

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HRID 1500843 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:17][CH2:18][CH2:19][S:20]([CH3:23])(=[O:22])=[O:21])[C:10](=O)OC(C)(C)C.[Cl:24][CH2:25]C([O-])=O.[Na+]>Cl>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]2[N:9]([CH2:17][CH2:18][CH2:19][S:20]([CH3:23])(=[O:22])=[O:21])[C:10]([CH2:25][Cl:24])=[N:1][C:2]=2[CH:7]=1

참가 물질

4

반응물 2

HCID 23665759Sodium chloroacetateHCID 89923659Tert-butyl 2-amino-4-chlorophenyl(3-(methylsulfonyl)propyl)carbamate

생성물 1

HCID 618081805-Chloro-2-(chloromethyl)-1-[3-(methylsulfonyl)propyl]-1H-benzimidazole수율 44%

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

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온도
100 °C

실험 절차

A mixture of tert-butyl 2-amino-4-chlorophenyl(3-(methylsulfonyl)propyl)carbamate (320 mg, 0.92 mmol) and sodium chloroacetate (130 mg, 1.1 mmol) in 4 N HCl was heated to 100° C. After overnight stirring, the reaction solution was cooled to RT and concentrated. The residue was diluted with DCM (100 mL) and washed with sat. NaHCO3 (50 mL). The organic layer was dried and concentrated under vacuum. The residue was purified by prep-TLC (DCM/EtOAc=3:1) to give 5-chloro-2-(chloromethyl)-1-(3-(methylsulfonyl)propyl)-1H-benzo[d]imidazole (130 mg, yield: 44%) as pale solid. MS obsd. (ESI+) [(M+H)+]: 321.0.

후처리

  1. temperaturethe reaction solution was cooled to RT
  2. concentrationconcentrated
  3. additionThe residue was diluted with DCM (100 mL)
  4. washwashed with sat. NaHCO3 (50 mL)
  5. customThe organic layer was dried
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by prep-TLC (DCM/EtOAc=3:1)

출처 및 근거

ORD 기록
ord-f546e6ba87dd442a95836d5b46375dab
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206191B2

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