Bis(trimethylsilyl)carbodiimide → HCID 178487045, compound
Reaction equation
[CH3:1][O:2][CH:3]1[CH2:25][CH2:24][C:6]2([CH2:14][C:13]3[C:8](=[CH:9][C:10]([C:15]4[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=4)[C:18]#[N:19])=[CH:11][CH:12]=3)[C:7]2=O)[CH2:5][CH2:4]1.C[Si]([N:30]=[C:31]=[N:32][Si](C)(C)C)(C)C>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[C:18]([C:17]1[CH:16]=[C:15]([C:10]2[CH:9]=[C:8]3[C:13](=[CH:12][CH:11]=2)[CH2:14][C:6]2([CH2:5][CH2:4][CH:3]([O:2][CH3:1])[CH2:25][CH2:24]2)/[C:7]/3=[N:32]\[C:31]#[N:30])[CH:22]=[CH:21][CH:20]=1)#[N:19]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 3-(4-methoxy-1′-oxo-1′,3′-dihydrospiro[cyclohexane-1,2′-indene]-6′-yl)benzonitrile (30 mg, 0.09 mmol) in CH2Cl2 (3 mL) was added TiCl4 (0.2 mL). It was stirred in microwave at 50° C. for 5 minutes. Then bis-trimethylsilylcarbodiimide (0.2 mL, 0.146 mmol) was added. The resulting mixture was stirred in microwave at 60° C. for 10 minutes. The reaction mixture was poured into ice-water, extracted with DCM. The combined organic phases were dried over anhydrous Na2SO4, and filtered. The filtrate was concentrated to give (E)-N-(5′-(3-cyanophenyl)-4-methoxyspiro[cyclohexane-1,2′-indene]-3′(1′H)-ylidene)cyanamide (30 mg, crude).
Workup
- stirringThe resulting mixture was stirred in microwave at 60° C. for 10 minutes
- extractionextracted with DCM
- dry with materialThe combined organic phases were dried over anhydrous Na2SO4
- filtrationfiltered
- concentrationThe filtrate was concentrated
Sources & evidence
- ORD record
- ord-c4fa577a499a49af8094f31c55e18773
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09212153B2
Reaction notes
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