Imidazole → HCID 21339421、化合物

HRID 368705ノート

反応式

HRID 368705 の反応式
[S:1](Cl)(Cl)=[O:2].N1C=CN=C1.[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][CH2:17][C@@H:18]([OH:21])[CH2:19][CH3:20]>ClCCl>[CH2:19]([C@@H:18]1[O:21][S:1](=[O:2])[N:16]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][N:10]=2)[CH2:17]1)[CH3:20]

参加物

5

反応物 3

HCID 795ImidazoleHCID 24386Thionyl ChlorideHCID 54335591HCID 54335591、化合物

生成物 1

HCID 21339421HCID 21339421、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

Thionyl chloride (18.98 millimoles) in dichloromethane (20 ml) is added dropwise to imidazole (4.7 g, 69 millimoles) in dichloromethane (50 ml) under argon. Then after 15 minutes the title compound of part (a) (17.26 millimoles) in 25 ml of dichloromethane was added slowly at a temperature maintained below 5° C. After an hour at a temperature range of 0° to 5° the temperature was allowed to warm up to room temperature. After 1 hour, water was added The organic layer was separated and the aqueous layer was subjected to extraction with dichloromethane. The combined organic portions were washed twice with water, dried (sodium sulphate) and evaporated to give the title compound as an orange oil (3.325 g, 15.66 millimoles), NMR data δ(400 MHz; CDCl3) 1.11 (1.5 H, t,J 8 Hz), 1.12 (1.5 H, t,J 8 Hz), 1.88-2.05 (1.5 H, m), 2.11-2.22 (0.5 H, m), 3.32 (0.5 H, dd, J 10 and 8 Hz), 3.74 (0.5 H, dd, J 10 and 7 Hz), 3.93-4.02 (1 H, m) 4.84-4.91 (0.5 H, m), 5.35-5.42 (0.5 H, m), 6.63 (0.5 H, d, J 8 Hz), 6.73 (0.5 H, d, j 8 Hz), 6.88-6.94 (1 H, m), 7.59-7.65 (1 H, m) and 8.25-8.30 (1 H, m).

出典と根拠

ORDレコード
ord-167c0ac9c0d0438f902ed09adf3149f2
出典データセット
uspto-grants-2000_10
特許番号
US06133449

反応ノート

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