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

HRID 969318Notes

Reaction equation

HRID 969318 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, 1 H), 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-3f590ffcfd05458fb0a5e11ef7bc8e05
Source dataset
uspto-grants-2007_12
Patent number
US07307075B2

Reaction notes

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