Ethyl isocyanatoacetate → HCID 43385182, compound

HRID 2223724Notes

Reaction equation

HRID 2223724 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:12])[CH:3]=1.[N:13]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:14]=[O:15]>C1COCC1>[CH2:20]([O:19][C:17](=[O:18])[CH2:16][NH:13][C:14]([NH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:12])[CH:3]=1)=[O:15])[CH3:21]

Participants

4

Reactant 2

HCID 76283Ethyl isocyanatoacetate2×HCID 811164-Amino-2-methylquinoline

Product 1

HCID 43385182HCID 43385182, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-14 °C

Procedure

A suspension of 4-amino-2-methylchinoline (4.0 g, 25.3 mmol) in dry THF (80 mL) is cooled to −14° C. and ethyl isocyanatoacetate (3.3 mL, 27.4 mmol) is added dropwise under vigourous stirring. The reaction is warmed to room temperature and stirred for 4 h. Further ethyl isocyanatoacetate (0.6 mL, 5 mmol) is added and the reaction mixture stirred for 15 h. The solvent is evaporated and the residue crystallized from CHCl3-heptane (1/5) to provide the title compound.

Workup

  1. temperatureThe reaction is warmed to room temperature
  2. stirringthe reaction mixture stirred for 15 h
  3. customThe solvent is evaporated
  4. customthe residue crystallized from CHCl3-heptane (1/5)

Sources & evidence

ORD record
ord-2fa02dafd3864ad2b1e0ede957813b2c
Source dataset
uspto-grants-2008_05
Patent number
US07375227B2

Reaction notes

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