Thiophosgene → n-(4-Tert-butylphenyl)-1-methyl-5-(trifluoromethyl)-1h-benzimidazol-2-amine

HRID 1594508노트

반응식

HRID 1594508 반응식
[C:1]([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:12]CN(C(C)C)C(C)C.C(Cl)(Cl)=S.[CH3:25][NH:26][C:27]1[C:28]([NH2:37])=[CH:29][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:31][CH:32]=1>C(Cl)Cl.[Cl-].[Na+].O.[Hg](OC(C(F)(F)F)=O)OC(C(F)(F)F)=O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([NH:9][C:25]2[N:26]([CH3:12])[C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:35])([F:34])[F:36])=[CH:29][C:28]=3[N:37]=2)=[CH:10][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

8

반응물 4

HCID 10040ThiophosgeneHCID 698614-Tert-ButylanilineHCID 81531Diisopropylethylamine2회HCID 715666N1-Methyl-4-(trifluoromethyl)benzene-1,2-diamine

생성물 1

HCID 68940748n-(4-Tert-butylphenyl)-1-methyl-5-(trifluoromethyl)-1h-benzimidazol-2-amine

시약·촉매·용매 3

HCID 16685285Hg(TFA)2촉매HCID 6344Dichloromethane용매2회HCID 57417360Sodium chloride; water용매

반응 조건

온도
40 °C

실험 절차

To a stirring solution of 4-t-butylaniline (1.3 mmol, 189 mg) and DIEA (2.53 mmol, 441 μL) in DCM (3 mL) at 0° C. was added dropwise thiophosgene (1.3 mmol, 91 μL). After 10 min the title compound of Example 6, Step B (10.5 mmol, 1.86 g) was added, and the reaction mixture was brought to 40° C. for 2 h. Hg(O2CCF3)2 (2.5 mmol, 1 g) and DIEA (1.3 mmol, 220 μL) were added and the reaction was heated at 40° C. for 16 h. The reaction was poured into DCM and brine containing Na2S, and the resulting slurry was filtered through celite. The organic phase was collected and dried over MgSO4 and concentrated in vacuo. Flash chromatography on silica eluting with 25% EtOAc in hexanes afforded the product as a yellow solid. LC-MS (ESI, Method B): 1.81 min, m/z 348.3 (M+1).

후처리

  1. additioncontaining Na2S
  2. filtrationthe resulting slurry was filtered through celite
  3. customThe organic phase was collected
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-9e1d39459f8d4b19af4167a1ea9ef6c8
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07301036B2

반응 노트

불러오는 중…