Thiophosgene → n-(4-Tert-butylphenyl)-1-methyl-5-(trifluoromethyl)-1h-benzimidazol-2-amine
Reaction equation
[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]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 40 °C
Procedure
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).
Workup
- additioncontaining Na2S
- filtrationthe resulting slurry was filtered through celite
- customThe organic phase was collected
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-9e1d39459f8d4b19af4167a1ea9ef6c8
- Source dataset
- uspto-grants-2007_11
- Patent number
- US07301036B2
Reaction notes
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