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

HRID 1986685Notes

Reaction equation

HRID 1986685 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[S: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[S:8][CH2:7][C:6]1=[O:15]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 68908573(S)-4-(3-Hydroxy-2-methylpropyl]-4H-benzo[1,4]thiazin-3-one

Product 1

HCID 68910017(S)-4-(3-Iodo-2-methylpropyl]-4H-benzo[1,4]thiazin-3-oneYield 75.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The compound (S)-4-(3-Hydroxy-2-methylpropyl]-4H-benzo[1,4]thiazin-3-one (108LM34-31) (2.33 g, 9.82 mmol), triphenylphosphine (5.15 g, 19.7 mmol), imidazole (1.67 g, 24.6 mmol) and iodine (7.48 g, 29.5 mmol) in CHCl3 (30 mL) were reacted according to GP4 to give the title compound (108LM37-34) (2.57 g, 75%). 1H NMR (CDCl3) δ 7.37 (d, J=7.8 Hz, 1H), 7.24 (t, J=7.8 Hz, 1H), 7.16 (d, J=7.8 Hz, 1H), 7.02 (t, J=7.8 Hz, 1H), 4.02 (d, J=6.8 Hz, CH2), 3.37 (s, CH2), 3.15-3.05 (m, CH2), 1.95 (m, 1H), 0.97 (d, J=6.2 Hz, CH3).

Sources & evidence

ORD record
ord-cdd7bf41edd3489ca146044317aa4999
Source dataset
uspto-grants-2009_06
Patent number
US07550459B2

Reaction notes

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