Carbon Disulfide → HCID 86642171, compound

HRID 1046956Notes

Reaction equation

HRID 1046956 reaction equation
[SH:1][CH2:2][CH2:3][CH2:4][Si:5]([O:10][CH3:11])([O:8][CH3:9])[O:6][CH3:7].[H-].[Na+].[C:14](=[S:16])=[S:15].Cl[CH2:18][C:19]#[N:20]>C(OCC)C>[C:14](=[S:1])([SH:16])[SH:15].[C:14](=[S:16])([S:1][CH2:2][CH2:3][CH2:4][Si:5]([O:10][CH3:11])([O:6][CH3:7])[O:8][CH3:9])[S:15][CH2:18][C:19]#[N:20]

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 7856ChloroacetonitrileHCID 20473(3-Mercaptopropyl)trimethoxysilaneHCID 24758Sodium hydride

Product 1

HCID 86642171HCID 86642171, compoundYield 106.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
7.5 °C

Procedure

(3-Mercaptopropyl)trimethoxysilane (1.97 g, 0.01 mol) was added within 10 minutes to a stirred suspension of sodium hydride (60% w/w, 0.42 g, 0.0175 mol) in dry diethyl ether (20 mL) whilst maintaining the reaction temperature between 5-10° C. The reaction mixture was then cooled to ˜0° C. when carbon disulfide (1.34 g, 0.012 mol) was added and the resulting mixture was kept at this temperature for one hour. Then α-Chloroacetonitrile (1.30 g, 0.017 mol) was added and the mixture was stirred at ambient temperature for a one hour. The reaction mixture was the filtered and the filtrate concentrated on rotary evaporator. Purification by chromatography on a short silica gel column (ethyl acetate: n-hexane 1:4) gave the title compound as a yellow liquid (2.25 g, 72%). 1H-nmr (CDCl3) δ 0.75 (m, 2H), 1.86 (m, 2H), 3.46 (t, 2H), 3.58 (s, 9H), 4.15 (s, 2H).

Workup

  1. additionwas added
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated on rotary evaporator
  4. customPurification by chromatography on a short silica gel column (ethyl acetate: n-hexane 1:4)

Sources & evidence

ORD record
ord-fb1795c0d354417a941b988870ead619
Source dataset
uspto-grants-2013_10
Patent number
US08569441B2

Reaction notes

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