Imidazole → Benzenamine, N,N-bis[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-
Reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][CH2:7][CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])=[CH:4][CH:3]=1.[C:19]1([N:25]([CH2:29][CH2:30][OH:31])[CH2:26][CH2:27][OH:28])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Si:32](Cl)([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33].N1C=CN=C1>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][CH2:8][O:9][Si:10]([C:13]([CH3:14])([CH3:15])[CH3:16])([CH3:11])[CH3:12])=[CH:17][CH:18]=1.[CH3:16][C:13]([Si:10]([CH3:11])([CH3:12])[O:28][CH2:27][CH2:26][N:25]([CH2:29][CH2:30][O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH3:14])[CH3:15]Participants
7
Reactant 4
Product 2
Reagents, catalysts & solvents 1
Procedure
A procedure analogous to that used for 1a was used with the following materials: 2,2'-(phenylimino)diethanol (9.0 g, 50 mmol), t-butyldimethylsilyl chloride (18.1 g, 0.12 mol), imidazole (17.0 g, 0.25 mol), and dimethylformamide (50 mL). The reaction was stirred overnight for convenience. Workup as in 1a gave 3a as a pale oil (21.6 g, >100%). 1H NMR (CDCl3) δ7.21 (2H, d, J=8.4), 6.68 (3H, overlapping d, t), 3.77 (4H, d, J=6.6), 3.52 (4H, d, J=6.6), 0.92 (18H, s), 0.06 (12H, s). 13C NMR (CDCl3) δ147.8, 129.2, 115.7, 111.4, 60.3, 53.5, 25.9, 18.3, -5.3. FDMS (m/e) 409 (M+). It was used as 100% without purification.
Sources & evidence
- ORD record
- ord-283a109238f7415b8d11cf40fece1e3b
- Source dataset
- uspto-grants-1997_11
- Patent number
- US05686254
Reaction notes
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