Methyl iodide → HCID 69416603, compound
Reaction equation
[CH2:1]([O:4][C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].[CH3:12]CN(C(C)C)C(C)C.C(Cl)(Cl)=S.[Cl:25][C:26]1[C:31]([Cl:32])=[CH:30][C:29]([NH2:33])=[C:28]([NH2:34])[CH:27]=1.CI>C(Cl)Cl.[Cl-].[Na+].O.CO>[CH2:1]([O:4][C:5]1[CH:11]=[CH:10][C:8]([NH:9][C:12]2[NH:33][C:29]3[CH:30]=[C:31]([Cl:32])[C:26]([Cl:25])=[CH:27][C:28]=3[N:34]=2)=[CH:7][CH:6]=1)[CH:2]=[CH2:3]Participants
9
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 40 °C
Procedure
To a stirring solution of the title compound of Example 14, Step A (2.5 mmol, 373 mmol) and DIEA (2.75 mmol, 478 μL) in CH2Cl2 (4 mL) at 0° C. was added thiophosgene (2.5 mmol, 191 μL). The solution was allowed to reach ambient temperature for 1 h, and 4,5-dichloro-1,2-phenylenediamine (2.5 mmol, 443 mg) was added to the reaction. The reaction mixture was heated to 40° C. for 16 h. MeI (5 mmol, 312 μL) was added, and the reaction was heated at 40° C. for 16 h. Aqueous workup with CH2Cl2 and brine, followed by flash chromatography on silica eluting with 3% MeOH in CH2Cl2 afforded the product as a brown solid. LC-MS (ESI, Method B): 1.79 min, m/z 334.1 (M+1).
Workup
- temperaturethe reaction was heated at 40° C. for 16 h
Sources & evidence
- ORD record
- ord-b89bb04097904303b8fd9c290f0e4d29
- Source dataset
- uspto-grants-2007_11
- Patent number
- US07301036B2
Reaction notes
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