Tert-Butylamine → Bis(t-butylamino)silacyclobutane

HRID 1621061Notes

Reaction equation

HRID 1621061 reaction equation
Cl[Si:2]1(Cl)[CH2:5][CH2:4][CH2:3]1.[C:7]([NH2:11])([CH3:10])([CH3:9])[CH3:8]>>[C:7]([NH:11][Si:2]1([NH:11][C:7]([CH3:10])([CH3:9])[CH3:8])[CH2:5][CH2:4][CH2:3]1)([CH3:10])([CH3:9])[CH3:8]

Participants

3

Reactant 2

HCID 6385Tert-Butylamine2×HCID 753731,1-Dichlorosilacyclobutane2×

Product 1

HCID 12029860Bis(t-butylamino)silacyclobutaneYield 45%

Procedure

Bis(t-butylamino)silacyclobutane (BTBSCB) was synthesized by reacting 1,1-dichlorosilacyclobutane with an excess amount of t-butylamine (Equation 1). To do so, 19.7 ml (0.166 mol) 1,1-dichlorosilacyclobutane was added to 105 ml (0.999 mol) t-butylamine in 1 L hexanes at 0° C. After bodying for three days at the room temperature, the reaction slurry was filtered to remove t-butylamine hydrochloride salt. The filtrant was vacuum dried to give a crude liquid product which was then vacuum distilled. 16 g Product was isolated at 99.2% purity in 45% yield at 71° C. under 50 torr pressure. The structure of the product analyzed with 1H, 13C and 29Si NMR, FT-IR and GC-MS was in consistence with bis(t-butylamino) silacyclobutane.

Workup

  1. filtrationthe reaction slurry was filtered
  2. customto remove t-butylamine hydrochloride salt
  3. customdried
  4. customto give a crude liquid product which
  5. distillationvacuum distilled

Sources & evidence

ORD record
ord-03c7bd37bef243b88761f4a924c996ed
Source dataset
uspto-grants-2014_07
Patent number
US08772524B2

Reaction notes

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