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

HRID 969318ノート

反応式

HRID 969318 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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).

出典と根拠

ORDレコード
ord-3f590ffcfd05458fb0a5e11ef7bc8e05
出典データセット
uspto-grants-2007_12
特許番号
US07307075B2

反応ノート

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