Dimethylformamide → 2-Formyl-4,5,6,7-tetrahydro-benzoimidazole-1-sulfonic acid dimethylamide

HRID 899641노트

반응식

HRID 899641 반응식
[CH3:1][N:2]([CH3:15])[S:3]([N:6]1[C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C:9]=2[N:8]=[CH:7]1)(=[O:5])=[O:4].C([Li])CCC.CN([CH:24]=[O:25])C.[NH4+].[Cl-]>C1COCC1>[CH3:1][N:2]([CH3:15])[S:3]([N:6]1[C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C:9]=2[N:8]=[C:7]1[CH:24]=[O:25])(=[O:4])=[O:5]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 69156673N,N-Dimethyl-4,5,6,7-tetrahydro-1H-benzimidazole-1-sulfonamideHCID 178418339Butyllithium

생성물 1

HCID 865903112-Formyl-4,5,6,7-tetrahydro-benzoimidazole-1-sulfonic acid dimethylamide수율 51.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

2-Formyl-4,5,6,7-tetrahydro-benzoimidazole-1-sulfonic acid dimethylamide was prepared following a modification of the procedure found in the Journal of Medicinal Chemistry, 40; 14, 1997, 2205. To a solution of 4,5,6,7-tetrahydro-benzoimidazole-1-sulfonic acid dimethylamide (2.67 g, 11.6 mmol) in dry THF (100 mL) under argon at −78° C. was added dropwise 2.5 M n-butyllithium in hexanes (7.0 mL, 17.5 mmol). The reaction was stirred at −78° C. for 1 hour, then DMF (1.1 mL, 13.9 mmol) was added dropwise, and the reaction was warmed to room temperature and stirred for 2 hours. Saturated NH4Cl (25 mL) was added, and the reaction mixture was concentrated, and then diluted with CH2Cl2 (500 mL) and distilled water (25 mL). The layers were separated and the aqueous phase was extracted with CH2Cl2 (2×100 mL). The combined organic extracts were washed with brine (1×100 mL), dried (Na2SO4), and concentrated. Purification of the crude material by column chromatography on silica gel (1:1 hexanes-EtOAc) provided 1.53 g (51%) of 2-formyl-4,5,6,7-tetrahydro-benzoimidazole-1-sulfonic acid dimethylamide as a yellow solid. 1H NMR (CDCl3) δ 1.82-1.86 (m, 4H), 2.66-2.68 (m, 2H), 2.86-2.88 (m, 2H), 2.96 (s, 6H), 9.99 (s, 1H).

후처리

  1. custom2-Formyl-4,5,6,7-tetrahydro-benzoimidazole-1-sulfonic acid dimethylamide was prepared
  2. temperaturethe reaction was warmed to room temperature
  3. stirringstirred for 2 hours
  4. concentrationthe reaction mixture was concentrated
  5. additiondiluted with CH2Cl2 (500 mL)
  6. distillationdistilled water (25 mL)
  7. customThe layers were separated
  8. extractionthe aqueous phase was extracted with CH2Cl2 (2×100 mL)
  9. washThe combined organic extracts were washed with brine (1×100 mL)
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated
  12. customPurification of the crude material by column chromatography on silica gel (1:1 hexanes-EtOAc)

출처 및 근거

ORD 기록
ord-4e7022fc7a4541c882b573cbce669d0d
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07354932B2

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