Butyl isocyanate → N-n-butyl-N'-octylurea triflate

HRID 487041Notes

Reaction equation

HRID 487041 reaction equation
[CH2:1]([NH2:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:10]([N:14]=[C:15]=[O:16])[CH2:11][CH2:12][CH3:13].[O-:17][S:18]([C:21]([F:24])([F:23])[F:22])(=[O:20])=[O:19].[Na+]>C(OCC)(=O)C.CO>[OH:20][S:18]([C:21]([F:24])([F:23])[F:22])(=[O:19])=[O:17].[CH2:10]([NH:14][C:15]([NH:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[O:16])[CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 3

HCID 8110Butyl isocyanateHCID 8143OctylamineHCID 23676748Sodium trifluoromethanesulfonate

Product 1

HCID 86747486N-n-butyl-N'-octylurea triflateYield 117.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
10 °C

Procedure

A four necked flask equipped with a thermometer, stirrer and drip funnel was charged with 2.58 g of octylamine and 200 g of ethyl acetate. To this was added dropwise a solution of 1.98 g of n-butylisocyanate in 30 g of ethyl acetate with stirring over 30 minutes while maintaining the inner temperature at 10° C. and allowed to react until the absorption of isocyanato group (2240 cm-1) disappeared IR spectrometrically. After dissolving the solidified reaction product in 50 g of methanol, a mixture of 2.086 g of 35% hydrochlonic acid and 50 g of methanol was added dropwise to the solution over 30 minutes and allowed to react at room temperature for 20 hours. Then a solution of 3.44 g of sodium triflate in 50 g of methanol was added dropwise over 30 minutes and allowed to react at room temperature for 20 hours. The reaction mixture was then filtered to remove NaCl by-product and evaporated to remove methano. 8.9 g of the title compound was obtained as a pale yellow liquid. This product is hereinafter referred to as "curing catalyst B". This product is soluble in aromatic hydrocarbon solvents such as toluene and xylene as well as esters such as butyl acetate and ethyl acetate.

Workup

  1. customA four necked flask equipped with a thermometer, stirrer and drip funnel
  2. customto react until the absorption of isocyanato group (2240 cm-1)
  3. additionwas added dropwise to the solution over 30 minutes
  4. customto react at room temperature for 20 hours
  5. customto react at room temperature for 20 hours
  6. filtrationThe reaction mixture was then filtered
  7. customto remove NaCl by-product
  8. customevaporated
  9. customto remove methano

Sources & evidence

ORD record
ord-63c0a54d82034da28ce8514b6ae6f5cd
Source dataset
uspto-grants-1994_03
Patent number
US05294582

Reaction notes

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