Triethylamine → 9-Chloro-1-(2,4-dichlorophenyl)-6-[(ethylsulfanyl)methyl]-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole

HRID 1399321노트

반응식

HRID 1399321 반응식
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=4[Cl:22])[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([CH2:23]O)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.C(N(CC)CC)C.[CH2:36]([S-:38])[CH3:37].[Na+]>CN(C)C=O.O1CCCC1.O.CC(O)C>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=4[Cl:22])[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([CH2:23][S:38][CH2:36][CH3:37])=[CH:4][CH:3]=1

참가 물질

9

반응물 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 4459711Sodium ethanethiolate2회HCID 57785885[9-Chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]methanol

생성물 1

HCID 577863759-Chloro-1-(2,4-dichlorophenyl)-6-[(ethylsulfanyl)methyl]-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole수율 65%

시약·촉매·용매 4

HCID 6228Dimethylformamide촉매HCID 962Water용매HCID 3776Isopropanol용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of [9-chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]methanol (300 mg, 0.784 mmol) and N,N-dimethylformamide (1 drop) in tetrahydrofuran (10 mL) was added thionyl chloride (0.086 mL, 1.18 mmol) at room temperature. The mixture was stirred at room temperature for 2 h. The mixture was concentrated in vacuo. To a solution of the residue in tetrahydrofuran (10 mL) and 2-propanol (10 mL) were added triethylamine (0.5 mL, 3.58 mmol) and sodium ethanethiolate (79.1 mg, 0.94 mmol) at room temperature. The mixture was stirred at 60° C. for 3 days. Sodium ethanethiolate (79.1 mg, 0.94 mmol) was added to the reaction mixture at room temperature and the mixture was stirred at 60° C. for 4 days. Water was added to the reaction mixture at room temperature and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was purified by flash chromatography on NH-silica gel eluting with a 10-40% ethyl acetate/n-hexane gradient mixture to give the title compound (216 mg, 0.506 mmol, 65%) as a colorless amorphous.

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. stirringThe mixture was stirred at 60° C. for 3 days
  3. stirringthe mixture was stirred at 60° C. for 4 days
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography on NH-silica gel eluting with a 10-40% ethyl acetate/n-hexane gradient mixture

출처 및 근거

ORD 기록
ord-bf0689f77cc84be4ab3005feb2bbb20d
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901141B2

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