Toluene → HCID 86735874, compound

HRID 1862956Notes

Reaction equation

HRID 1862956 reaction equation
C[C:2]1[CH2:6][CH2:5][CH2:4][Si:3]=1Cl.[C:8]1(C)C=CC=CC=1.[C:15]1(=[O:22])[NH:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1>C(N(CC)CC)C>[CH3:8][C:16]1([Si:3]2[CH2:4][CH2:5][CH2:6][CH:2]=2)[CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:15]1=[O:22]

Participants

5

Reactant 3

HCID 1140TolueneHCID 7768CaprolactamHCID 20392807HCID 20392807, compound

Product 1

HCID 86735874HCID 86735874, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Methylsilacyclopentenyl chloride, 1 mol, was added over a period of 30 minutes to an anhydrous solution of 750 ml. of toluene, 146 g. of triethylamine and 1.05 mol of epsilon-caprolactam in a flask. After 1 hour of stirring the reaction mixture was filtered to remove (CH3CH2)3N.HCl and the filtrate was fractionally distilled to give a moderate yield of methylsilacyclopentenyl-epsilon-caprolactam, b.p.=120° to 140° C. at approximately 0.5 kilopascals of pressure. Infra-red spectroscopy indicated that the bonding in this silyl lactam, between the methylsilacyclopentenyl radical and the epsilon-caprolactamo radical, is predominently silicon-nitrogen bonding.

Workup

  1. filtrationwas filtered
  2. customto remove (CH3CH2)3N.HCl
  3. distillationthe filtrate was fractionally distilled

Sources & evidence

ORD record
ord-7911cd3fa1d9469cad051996ccbec7fd
Source dataset
uspto-grants-1979_09
Patent number
US04167511

Reaction notes

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