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

HRID 1500843ノート

反応式

HRID 1500843 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f546e6ba87dd442a95836d5b46375dab
出典データセット
uspto-grants-2015_12
特許番号
US09206191B2

反応ノート

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