Hydrochloric Acid → HCID 86748102, compound

HRID 2225467Notes

Reaction equation

HRID 2225467 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].Cl.[F:18][B-:19]([F:22])([F:21])[F:20].[Na+]>C(OCC)(=O)C.CO>[F:18][B-:19]([F:22])([F:21])[F:20].[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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8110Butyl isocyanateHCID 8143OctylamineHCID 4343483Sodium Tetrafluoroborate

Product 1

HCID 86748102HCID 86748102, compoundYield 97%

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% hydrochloric 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 2.2 g of sodium tetrafluoroborate 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 the solvent. 6.1 g of the title compound was obtained as a pale yellow liquid.

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 the solvent

Sources & evidence

ORD record
ord-ced118bd0cb04c74b302491aa862426d
Source dataset
uspto-grants-1994_09
Patent number
US05344890

Reaction notes

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