p-Tolunitrile → HCID 57956268, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)=[NH:11])[CH:6]=[CH:7][CH:8]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C1(C)C=CC(C#N)=CC=1.C[O:39][C:40]1C=C(C=[CH:45][CH:46]=1)N.[O:47]1CCCC1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:9]2[CH:45]=[C:46]([C:40]([OH:39])=[O:47])[N:11]=[C:10]2[C:12]2[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=2)[CH:6]=[CH:7][CH:8]=1Participants
Procedure
N-(3-Methoxyphenyl)-4-methylbenzenecarboxamidine To a solution of 2.5 mL (5.0 mmol) of 2.0 M (in tetrahydrofuran) sodium bis(trimethylsilyl)amide in 10 mL of tetrahydrofuran at ambient temperature was added a solution of 0.59 g (5.0 mmol) of p-tolunitrile in 20.0 mL of tetrahydrofuran and the resulting solution was stirred for 30 min. To this reaction mixture was slowly added 0.56 mL (5.0 mmol) of 3-methoxyaniline. The resulting mixture was stirred at ambient temperature overnight and then poured into ice/water (25 mL) and extracted with dichloromethane (50 mL). The organic layer was separated and the aqueous layer was extracted with dichloromethane (25 mL). The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo to yield the title compound as yellow solid which was used without further purification. LC/MS 241.1 (M+1).
Workup
- stirringThe resulting mixture was stirred at ambient temperature overnight
- extractionextracted with dichloromethane (50 mL)
- customThe organic layer was separated
- extractionthe aqueous layer was extracted with dichloromethane (25 mL)
- dry with materialThe combined organic layers were dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-f22027802efc41dfac5585bcc8226bdd
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07759352B2
Reaction notes
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