Propyl isocyanate → HCID 18430533, compound

HRID 1278544Notes

Reaction equation

HRID 1278544 reaction equation
[CH2:1]([N:4]=[C:5]=[O:6])[CH2:2][CH3:3].[F:7][C:8]1[C:21]([NH2:22])=[CH:20][C:11]2[N:12]([CH2:17][C:18]#[CH:19])[C:13](=[O:16])[CH2:14][O:15][C:10]=2[CH:9]=1>O1CCOCC1>[CH2:1]([NH:4][C:5]([NH:22][C:21]1[C:8]([F:7])=[CH:9][C:10]2[O:15][CH2:14][C:13](=[O:16])[N:12]([CH2:17][C:18]#[CH:19])[C:11]=2[CH:20]=1)=[O:6])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 61033Propyl isocyanate2×HCID 111603236-amino-7-fluoro-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-3-one

Product 1

HCID 18430533HCID 18430533, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

n-Propyl isocyanate (1.0 g, 11.7 mmol) was added to a solution of 7-fluoro-6-amino-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-one (0.20 g, 0.9 mmol) in dioxane (20 mL) with stirring. The reaction mixture was heated to 80° C. for 4 hours. More n-propyl isocyanate (0.43 g, 5 mmol) was added and the reaction mixture was maintained at 80° C. overnight. Then the solution was concentrated to dryness to afford N-n-propyl-N′-[7-fluoro-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-one-6-yl]urea as a crude intermediate (1.1 g). This was used for the next step without further purification.

Workup

  1. temperaturethe reaction mixture was maintained at 80° C. overnight
  2. concentrationThen the solution was concentrated to dryness

Sources & evidence

ORD record
ord-4812db38ef61436287b769a9dc9938de
Source dataset
uspto-grants-2002_09
Patent number
US06444615B1

Reaction notes

Loading…