Dichloromethane → 1-Phenyltriazolylmethyl-3-hydroxypyridine-2-thione

HRID 539528

反応式

HRID 539528 の反応式
[C:1]1([N:7]2[CH:12]=[CH:11][C:10]([CH2:13][C:14]3[N:15]=[N:16][NH:17][CH:18]=3)=[C:9]([O:19]C)[C:8]2=[S:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B(Br)(Br)Br.C(Cl)Cl>>[C:1]1([N:7]2[CH:12]=[CH:11][C:10]([CH2:13][C:14]3[N:15]=[N:16][NH:17][CH:18]=3)=[C:9]([OH:19])[C:8]2=[S:21])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

4

反応物 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 1784876431-Phenyltriazolylmethyl-3-methoxypyridine-2-thione

生成物 1

HCID 1785157291-Phenyltriazolylmethyl-3-hydroxypyridine-2-thione収率 67.3%

実験手順

Reaction of 153a (0.28 g, 0.93 mmol) and 1M BBr3 in CH2Cl2 (1.5 equiv) within 48 h as described for the synthesis of 148a gave compound 154a (0.178 g, 67%) as olive green solid. 1H NMR (400 MHz, CDCl3) δ 8.43 (d, J=16.6 Hz, 1H), 8.39 (s, 1H), 7.79 (dd, J=6.6, 1.3 Hz, 1H), 7.69 (m, 2H), 7.46 (m, 3H), 6.97 (dd, J=7.7, 1.2 Hz, 1H), 6.69 (dd, J=7.6, 6.8 Hz, 1H), 5.94 (s, 2H). 13C NMR (100 MHz, CDC3) δ 168.59, 155.12, 141.60, 136.66, 131.65, 129.69, 128.99, 122.57, 120.60, 114.04, 112.47, 77.30, 76.99, 76.67, 52.08. HRMS (EI) calcd for C14H12N4OS [M]+ 284.0730. found 284.0732.

出典と根拠

ORDレコード
ord-a4d8c3f230314695992f9ea23d163ebf
出典データセット
uspto-grants-2014_10
特許番号
US08871728B2

関連ノート

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