Nitrogen → HCID 87104175, compound

HRID 2190233Notes

Reaction equation

HRID 2190233 reaction equation
N#N.[C:3]([CH2:22][CH2:23][S:24][CH2:25][CH2:26][NH2:27])([C:6]([C:9]([C:12]([C:15]([C:18]([F:21])([F:20])[F:19])([F:17])[F:16])([F:14])[F:13])([F:11])[F:10])([F:8])[F:7])([F:5])[F:4].CN(C)C.Cl[C:33](OCC)=[O:34].C[Si](Cl)(Cl)Cl>C1(C)C=CC=CC=1.C(N(CC)CC)C>[C:3]([CH2:22][CH2:23][S:24][CH2:25][CH2:26][N:27]=[C:33]=[O:34])([C:6]([C:9]([C:12]([C:15]([C:18]([F:19])([F:20])[F:21])([F:16])[F:17])([F:14])[F:13])([F:11])[F:10])([F:8])[F:7])([F:5])[F:4]

Participants

8

Reactant 5

HCID 947NitrogenHCID 1146TrimethylamineHCID 6399TrichloromethylsilaneHCID 10928Ethyl chloroformateHCID 857914472-[(3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluorooctyl)thio]ethanamine

Product 1

HCID 87104175HCID 87104175, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

In a 500 mL three neck flask (with mechanical stirrer, temperature probe, dropping funnel —N2), containing dry toluene (350 mL), one equivalent of each of the C6F13C2H4SCH2CH2NH2 (0.1 mol) and trimethyl amine (0.1 mol) were added. The mixture was cooled to 0° C. Ethyl chloroformate (0.11 mol) was added dropwise within 20 min. The mixture was allowed to warm to room temperature while stirring was continued. A second equivalent of triethyl amine was added followed by the dropwise addition of methyl trichlorosilane (0.12 mol) at 30-40° C. (addition time about 20-30 min). The dropping funnel was replaced with a reflux condenser. The mixture was heated to 100° C. for 1 h (less than the reflux temperature of toluene). After the mixture was cooled to ambient temperature the precipitated ammonium salts were filtered into a flask using a glass frit. Under steady N2 flow, both toluene and generated ethoxy methyl dichlorosilane were distilled off at 200 mm Hg (266.6×102 Pa). The collected organic by-product was treated with dilute aqueous bicarbonate solution to quench the silane. The residue was dried at 2 mm Hg (2.67×102 Pa) using a dry-ice cooled trap to furnish C6F13C2H4SCH2CH2NCO in 95% yield as a light red-brown liquid.

Workup

  1. additionwere added
  2. temperatureto warm to room temperature
  3. addition(addition time about 20-30 min)
  4. customThe dropping funnel was replaced with a reflux condenser
  5. filtrationwere filtered into a flask
  6. distillationwere distilled off at 200 mm Hg (266.6×102 Pa)
  7. additionThe collected organic by-product was treated with dilute aqueous bicarbonate solution
  8. customto quench the silane
  9. customThe residue was dried at 2 mm Hg (2.67×102 Pa)

Sources & evidence

ORD record
ord-8f357c6cdffc45e180841d1551a6031a
Source dataset
uspto-grants-2012_12
Patent number
US08324314B2

Reaction notes

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