Tert-Butylamine → 1-(Tert-butylamino)-2-(tetramethylcyclopentadienyl)-1,1,2,2-tetramethyldisilane

HRID 393306Notes

Reaction equation

HRID 393306 reaction equation
Cl[Si:2]([CH3:16])([CH3:15])[Si:3]([CH:6]1[C:10]([CH3:11])=[C:9]([CH3:12])[C:8]([CH3:13])=[C:7]1[CH3:14])([CH3:5])[CH3:4].[C:17]([NH2:21])([CH3:20])([CH3:19])[CH3:18]>CCOCC>[C:17]([NH:21][Si:2]([CH3:16])([CH3:15])[Si:3]([CH:6]1[C:10]([CH3:11])=[C:9]([CH3:12])[C:8]([CH3:13])=[C:7]1[CH3:14])([CH3:5])[CH3:4])([CH3:20])([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 1317203731-Chloro-2-(tetramethylcyclopentadienyl)-1,1,2,2-tetramethyldisilane

Product 1

HCID 1317203741-(Tert-butylamino)-2-(tetramethylcyclopentadienyl)-1,1,2,2-tetramethyldisilane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3.000 g (11.0 mmol) 1-chloro-2-(tetramethylcyclopentadienyl)-1,1,2,2-tetramethyl-disilane in 50 mL ether was added 2.422 g (33.1 mmol) tert-butylamine. Precipitate formed rapidly. The slurry was stirred for several days at room temperature, then was gently heated to drive the reaction to completion. The solvent was removed, the residue was extracted with pentane, the amine hydrochloride was filtered and the pentane was removed under reduced pressure to give the product as a yellow oil. The yield was 3.150 (92.5%). Mass spec: m/e 309. 1H NMR (C6D6) δ 2.75 (s, 1H), 1.95 (s, 6H), 1.82 (s, 6H),1.08 (s, 9H), 0.51 (s, 1H), 0.24 (s, 6H), 0.16 (s, 6H); 13C NMR (C6D6) δ 135.2, 134.4, 55.2, 50.3, 34.1, 14.9 11.6, 3.3, −1.4.

Workup

  1. customPrecipitate formed rapidly
  2. temperaturewas gently heated
  3. customthe reaction to completion
  4. customThe solvent was removed
  5. extractionthe residue was extracted with pentane
  6. filtrationthe amine hydrochloride was filtered
  7. customthe pentane was removed under reduced pressure

Sources & evidence

ORD record
ord-0f63c1f4d599454c92595212d91d4ef5
Source dataset
uspto-grants-2004_10
Patent number
US06806326B2

Reaction notes

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