Trichloromethanethiol → 3-(4-Bromophenyl)-5-chloro-1,2,4-thiadiazole

HRID 1436443ノート

反応式

HRID 1436443 の反応式
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[NH:11])[NH2:10])=[CH:5][CH:4]=1.C(N(CC)CC)C.[Cl:19][C:20]([SH:23])(Cl)Cl>C(Cl)Cl>[Br:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:20]([Cl:19])[S:23][N:11]=2)=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 6390TrichloromethanethiolHCID 8471TriethylamineHCID 122077144-Bromobenzene-1-carboximidamide--hydrogen chloride (1/1)

生成物 1

HCID 118326413-(4-Bromophenyl)-5-chloro-1,2,4-thiadiazole収率 28%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

4-Bromobenzenecarboximidamide hydrochloride (1.00 g, 4.25 mmol), prepared in the previous step, was suspended in methylene chloride (25 mL) and triethylamine (6.1 mL, 42.5 mmol) was added and the mixture was cooled to 0° C. Perchloromethyl mercaptan (0.47 g, 4.25 mmol) was added slowly, the mixture was stirred for 30 min, warmed to 25° C. and stirred 4 h. The mixture was diluted with methylene chloride, filtered through the Celite™ reagent, and concentrated. Flash chromatography (2% acetone in hexane) afforded 3-(4-bromophenyl)-5-chloro-1,2,4-thiadiazole (327 mg, 28%). HRMS: calcd for C8H4BrClN2S, 273.89671; found (EI, M+.), 273.8968; Analytical HPLC: purity 100% at 210-370 nm, 11.2 min; 100% at 272 nm, 11.2 min; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min.

後処理

  1. temperaturewarmed to 25° C.
  2. stirringstirred 4 h
  3. filtrationfiltered through the Celite™ reagent
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-67a846e3c7184bf68bc721306029be22
出典データセット
uspto-grants-2009_11
特許番号
US07618990B2

反応ノート

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