N-(1-adamantyl)-N-(trimethylsilyl)benzeneamine → N,N'-Bis(1-adamantyl)-N,N'-diphenylformamidinium chloride

HRID 41659Notes

Reaction equation

HRID 41659 reaction equation
[Cl-:1].[C:2]([N:6]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:7]=[N+:8]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:5])([CH3:4])[CH3:3].[C:25]12(N([Si](C)(C)C)C3C=CC=CC=3)[CH2:34][CH:29]3CC(C[CH:27]([CH2:28]3)[CH2:26]1)C2>>[Cl-:1].[C:15]12([N:8]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:7]=[N+:6]([C:2]34[CH2:3][CH:11]5[CH2:12][CH:13]([CH2:14][CH:9]([CH2:10]5)[CH2:5]3)[CH2:4]4)[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:18][CH:27]3[CH2:28][CH:29]([CH2:34][CH:25]([CH2:26]3)[CH2:17]1)[CH2:16]2

Participants

3

Reactant 2

HCID 66604537N-(1-adamantyl)-N-(trimethylsilyl)benzeneamineHCID 66607390N,N'-Bis(tert-butyl)-N,N'-diphenylformamidinium chloride

Product 1

HCID 66607202N,N'-Bis(1-adamantyl)-N,N'-diphenylformamidinium chlorideYield 71.5%

Procedure

With the same method used in the synthesis of 4a except for adding 3b (2 equiv), 4b (71.5%) was obtained as a white solid. 1H NMR (300 MHz, CD2Cl2) δ=8.71 (s, 1H), 7.24-6.90 (m, 6H), 6.78 (d, J=7.4 Hz, 4H), 2.21 (br. s, 6H), 2.07-1.99 (m, 12H), 1.66 (br. s, 12H); 13C NMR (75 MHz, CD2Cl2) δ 152.7, 135.0, 130.3, 129.0, 128.9, 66.6, 41.8, 35.4, 30.5. HRMS-DART (m/z): [M]+ calcd for C33H41ClN2, 465.3264. found, 465.3249.

Sources & evidence

ORD record
ord-ecdc60035b6442eea51e1fd337640f3e
Source dataset
uspto-grants-2013_09
Patent number
US08530687B2

Reaction notes

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