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

HRID 2102515Notes

Reaction equation

HRID 2102515 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-958fff5a1c4f4c0abba00fb5f0f28979
Source dataset
uspto-grants-2009_08
Patent number
US07576078B2

Reaction notes

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