Triethoxy(3-isocyanatopropyl)silane → HCID 53869758, compound

HRID 1941021Notes

Reaction equation

HRID 1941021 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][Si:7]([O:14][CH2:15][CH3:16])([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10])=[C:2]=[O:3].[CH:17]1([OH:33])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH:25]=[CH:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.C1(=O)CCCCCCCC=CCCCCCC1.[BH4-].[Na+].[N-]=C=O>C(O)C.C(N(CC)CC)C>[CH2:12]([O:11][Si:7]([O:14][CH2:15][CH3:16])([O:8][CH2:9][CH3:10])[CH2:6][CH2:5][CH2:4][NH:1][C:2](=[O:3])[O:33][CH:17]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH:25]=[CH:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[CH3:13]

Participants

8

Reactant 5

HCID 90613Triethoxy(3-isocyanatopropyl)silaneHCID 105034IsocyanateHCID 5346348-Cyclohexadecen-1-oneHCID 4311764Sodium borohydrideHCID 53721826HCID 53721826, compound

Product 1

HCID 53869758HCID 53869758, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

1 ml of 3-isocyanatopropyltriethoxysilane and 50 mg of triethylamine are added to 0.9 g of 8-cyclohexadecen-1-ol, prepared by reduction of 8-cyclohexadecen-1-one using NaBH4 in ethanol, and the mixture is kept at 80° C. for 24 hours. Low-boiling components are removed at 90° C./0.1 mbar. The residue solidifies on cooling to form a wax and shows only traces of an isocyanate band in the IR spectrum, but instead a strong band (1700 cm-1) of the ##STR5## 5.2(m, 2H, --CH=CH--); 0.6 (m, --CH2Si).

Workup

  1. customLow-boiling components are removed at 90° C./0.1 mbar
  2. temperatureon cooling
  3. customto form a wax

Sources & evidence

ORD record
ord-083132ec92c44138bd75802dcf0f1929
Source dataset
uspto-grants-1997_12
Patent number
US05702777

Reaction notes

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