Quinoline → HCID 22234884, compound

HRID 2415630Notes

Reaction equation

HRID 2415630 reaction equation
Cl[C:2]([O:4][CH2:5][CH:6]([CH3:8])[CH3:7])=[O:3].[S-:9][C:10]#[N:11].N1C2C(=CC=CC=2)C=CC=1.C([O-])([O-])=O.[Na+].[Na+]>O>[CH2:5]([O:4][C:2]([N:11]=[C:10]=[S:9])=[O:3])[CH:6]([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 7047QuinolineHCID 9322ThiocyanateHCID 10340Sodium CarbonateHCID 62365Isobutyl chloroformate

Product 1

HCID 22234884HCID 22234884, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
27.5 °C

Procedure

136.58 grams (1 mole) of 99% isobutyl chloroformate are added to a 50% thiocyanate solution containing 81 grams (1 mole) of NaSCN, 81 grams of water, 4.36 grams of quinoline (catalyst) and 1.8 grams of Na2CO3 (base) while maintaining a reaction temperature of 25-30° C. with agitation. The reaction is monitored for the consumption of the chloroformate during the formation of an upper layer of isobutoxycarbonyl isothiocyanate (approximately 4 hours). The contents of the reaction vessel are filtered to remove solid sodium chloride and the isobutoxycarbonyl isothiocyanate is isolated in the form of a layer that separates from the aqueous layer.

Workup

  1. customThe reaction is monitored for the consumption of the chloroformate during the formation of an upper layer of isobutoxycarbonyl isothiocyanate (approximately 4 hours)
  2. filtrationThe contents of the reaction vessel are filtered
  3. customto remove solid sodium chloride

Sources & evidence

ORD record
ord-4caaf0604c9f4180964a3cfb285bb332
Source dataset
uspto-grants-2004_11
Patent number
US06820746B2

Reaction notes

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