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

HRID 1191349ノート

反応式

HRID 1191349 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, 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).

出典と根拠

ORDレコード
ord-c76d3b15183b4ce4acf3ca4c429e448d
出典データセット
uspto-grants-2014_03
特許番号
US08680115B2

反応ノート

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