Imidazole → (R)-4-(3-Iodo-2-methylpropyl]-4H-benzo[1,4]oxazin-3-one

HRID 1191348Notes

Reaction equation

HRID 1191348 reaction equation
O[CH2:2][C@H:3]([CH3:16])[CH2:4][N:5]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH2:7][C:6]1=[O:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:41]I>C(Cl)(Cl)Cl>[I:41][CH2:2][C@H:3]([CH3:16])[CH2:4][N:5]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH2:7][C:6]1=[O:15]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 68910321(R)-4-(3-Hydroxy-2-methylpropyl]-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 68908541(R)-4-(3-Iodo-2-methylpropyl]-4H-benzo[1,4]oxazin-3-oneYield 20%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Crude (R)-4-(3-hydroxy-2-methylpropyl]-4H-benzo[1,4]oxazin-3-one (108LM40-37) (1.040 g), triphenylphosphine (0.99 g, 3.77 mmol), imidazole (0.32 g, 4.71 mmol) and iodine (1.43 g, 5.65 mmol) in CHCl3 (30 mL) were reacted according to GP4 to give the crude title compound (108LM46-43) (0.312 g).

Sources & evidence

ORD record
ord-0dda117bf5924278a838368ecf0c502c
Source dataset
uspto-grants-2014_03
Patent number
US08680115B2

Reaction notes

Loading…