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

HRID 2103174Notes

Reaction equation

HRID 2103174 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-a08f042162474c81874e9588320dc5b8
Source dataset
uspto-grants-2009_08
Patent number
US07576100B2

Reaction notes

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