Benzoyl isothiocyanate → HCID 86706796, compound

HRID 876102Notes

Reaction equation

HRID 876102 reaction equation
[C:1]([N:9]=[C:10]=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:12][CH2:13][CH2:14][CH2:15][Si:16]([O:21][CH3:22])([O:19][CH3:20])[O:17][CH3:18]>ClCCl>[CH2:15]([Si:16]([O:21][CH3:22])([O:19][CH3:20])[O:17][CH3:18])[CH2:14][CH3:13].[C:1]([NH:9][C:10]([NH2:12])=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 83756Aminopropyltrimethoxysilane

Product 1

HCID 86706796HCID 86706796, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 250 mL 3-neck RBF equipped with a condenser, magnetic stirrer, thermo-probe, nitrogen purge and pressure-equilibrated addition funnel was added benzoyl isothiocyanate (25.0 g, 0.150 mol) followed by dichloromethane (100 mL). The reaction mixture was cooled in an ice-water bath to a temperature below 5° C., at which point 3-aminopropyl trimethoxysilane (27.7 g, 0.150 mol) and dichloromethane (100 mL) were added slowly over a period of time of 30 minutes. The ice-water bath was removed and the reaction mixture was stirred at room temperature under a nitrogen purge overnight. The reaction mixture was then concentrated in vacuo at a temperature of 40° C. to provide a clear red liquid. The liquid was dried to constant weight in vacuo at a temperature of 50° C. and a pressure of <1 mTorr in a 97% yield.

Workup

  1. customTo a 250 mL 3-neck RBF equipped with a condenser, magnetic stirrer
  2. customthermo-probe, nitrogen purge
  3. additionwere added slowly over a period of time of 30 minutes
  4. customThe ice-water bath was removed
  5. custompurge overnight
  6. concentrationThe reaction mixture was then concentrated in vacuo at a temperature of 40° C.
  7. customto provide a clear red liquid
  8. customThe liquid was dried to constant weight in vacuo at a temperature of 50° C.

Sources & evidence

ORD record
ord-af598700f1474089bd99f31c96eca2bd
Source dataset
uspto-grants-2015_03
Patent number
US08986847B2

Reaction notes

Loading…